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Advances in the field of adrenal cortical hormones

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Zusammenfassung

Aus den Arbeiten der letzten zwei Jahre auf dem Gebiet der Nebennierenrinden-Hormone stechen — was die Herstellung neuer, hochwirksamer Verbindungen anbetrifft — die Isolierung und Konstitutionsaufklärung des natürlichen Hormons Aldosteron und die synthetische Gewinnung der 9α-halogenierten Hydrocortisone hervor. Diese Ergebnisse haben den Weg zu weiteren wesentlichen Entwicklungen eines Gebietes geöffnet, das mit Cortison und Hydrocortison abgeschlossen schien.

Auf dem Gebiete der Teilsynthese wurde die Herstellung von 11-oxygenierten aus 12-oxygenierten Derivaten und insbesondere aus Verbindungen ohne Sauerstoff im Ring C stark ausgebaut. Bei der letzteren liegen die wichtigsten Befunde wohl in den mikrobiologischen Hydroxylierungen in 11-Stellung und den anschliessenden chemischen Umwandlungen. Erst kürzlich ist es möglich geworden, auch die typischen Seitenketten durch mikrobiologische Methoden zu gewinnen.

Die Totalsynthese der Hormone aus einfachsten chemischen Bausteinen wurde entwickelt und macht rasche Forschritte. Die Auffassungen über die Biosynthese haben konkretere Formen angenommen. Die unzähligen Arbeiten über Katabolismus und klinische Verwendung der Nebennierenrinden-Hormone konnten im Rahmen dieser Übersicht nicht einmal gestreift werden.

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References

  1. C. W. Shoppee andE. Shoppee, inRood,Chemistry of Carbon Compounds, Vol. II B (Amsterdam, 1953) p. 929.

  2. C. W. Shoppee, Ann. Rev. Biochem.22, 261 (1953).

    Article  CAS  Google Scholar 

  3. B. A. Hems, J. Pharmacy Pharmacol. (Brit.)5, 409 (1953).

    Article  CAS  Google Scholar 

  4. C. Djerassi, Vitamins and Hormones11, 205 (1953).

    Article  CAS  Google Scholar 

  5. G. Rosenkranz andF. Sondheimer, Progr. Chem. Org. Natur. Prod.10, 274 (1953).

    CAS  Google Scholar 

  6. L. T. Samuels andH. Reich, Ann. Rev. Biochem.21, 129 (1952).

    Article  CAS  Google Scholar 

  7. H. J. Staudinger, inL. Weissbecker,Probleme des Hypophysen-Nebennierenrindensystems (Berlin, 1953), p. 1.

  8. J. Zander, Klin. Wschr.30, 873 (1952).

    Article  CAS  Google Scholar 

  9. R. I. Dorfman andF. Ungar,Metabolism of Steroid Hormones, (Minneapolis, 1953).

  10. G. Pincus, Rec. Progr. Hormone Res.7–9 (New York, 1952–1954).

  11. Ciba Foundation Colloquia on Endocrinology, 4:Water Metabolism, 5:Bioassay, 6:Carbohydrate Metabolism, 7:Synthesis and Metabolism of Adrenocortical Steroids (London, 1952–1953).

  12. R. Neher andA. Wettstein, unpublished data.

  13. I. E. Bush, Ciba Found. Colloquia on Endocrinol.5, 203 (1953);7, 210 (1953); J. Endocrinol.9, 95 (1953).

    Google Scholar 

  14. I. I. Salamon andK. Dobriner, J. Clin. Endocrinol.12, 967 (1952).

    Google Scholar 

  15. K. Dobriner, E. R. Katzenellenbogen, andR. Schneider, Arch. Biochem. Biophys.48, 167 (1954).

    Article  CAS  Google Scholar 

  16. A. Wettstein, F. W. Kahnt, andR. Neher, Ciba Foundation Colloquia on Endocrinol.8 (1954), in press; compare literature cited therein.

  17. W. J. Haines, Rec. Progr. Hormone Res.7, 255 (1952).

    Google Scholar 

  18. K. Dobriner, E. R. Katzenellenbogen, andR. Schneider, Arch. Biochem. Biophys.48, 167 (1954).

    Article  CAS  Google Scholar 

  19. H. Levy andSt. Kushinsky, Rec. Progr. Hormone Res.9, 357 (1954).

    Google Scholar 

  20. D. H. Nelson andL. T. Samuels, Rec. Progr. Hormone Res.9, 377 (1954); J. Clin. Endocrinol. Metabol.12, 519 (1952).

    Google Scholar 

  21. K. Eik-Nes, D. H. Nelson, andL. T. Samuels, J. Clin. Endocrinol. Metabol.13, 1280 (1953). Modification see:R. I. S. Bayliss andA. W. Steinbeck, Mem. Soc. Endocrinol.2, 31 (1953).

    Article  CAS  Google Scholar 

  22. I. E. Bush, Ciba Found. Colloquia on Endocrinol.5, 203 (1953);7, 210 (1953); J. Endocrinol.9, 95 (1953); J. biol. Chem.205, 783 (1953).

    Google Scholar 

  23. C. J. O. R. Morris andD. C. Williams, Ciba Found. Colloquia on Endocrinol.7, 261 (1953).

    Google Scholar 

  24. L. T. Samuels,Endocrinological Symposium, Marburg, June1954 (Method compare4).

  25. G. W. Thorn, Meeting Swiss Society for Endocrinology, Zurich, July 1954.

  26. R. H. Johnson andW. J. Haines, Science116, 456 (1952).

    Article  CAS  Google Scholar 

  27. C. de Courcy, C. H. Gray, andJ. B. Lunnon, Nature170, 494 (1952).

    Article  Google Scholar 

  28. K. Eik-Nes, J. A. Schellman, R. Lumry andL. T. Samuels, J. biol. Chem.206, 411 (1954).

    Article  CAS  Google Scholar 

  29. L. Ya. Areshkina, B. N. Bukin andE. P. Skorobogatova, Biokhim.18, 559 (1953).

    CAS  Google Scholar 

  30. R. Klein, C. Papadatos, J. Fortunato, andC. Byers, J. Clin. Endocrinol.14, 815 (1954).

    Article  Google Scholar 

  31. Compare lately:J. J. Schneider, J. biol. Chem.194, 337 (1952);C. L. Cope andB. Hurlock, Memoirs Soc. Endocrinol.2, 25 (1953).

    Article  CAS  Google Scholar 

  32. Cope andHurlock, loc. cit. ; For guinea pigs compare lately:S. Burstein andR. I. Dorfman, J. biol. Chem.206, 607 (1954); Feder. Proc.13, 188 (1954).

    Google Scholar 

  33. Reviews see:W. J. Haines, Rec. Progr. Hormone Res.7, 268 (1952).

    Google Scholar 

  34. A. Zaffaroni, Rec. Progr. Hormone Res.8, 51 (1953).

    Google Scholar 

  35. K. Savard, Rec. Progr. Hormone Res.9, 185 (1954).

    Google Scholar 

  36. K. H. Pfeffer andHj. Staudinger, Z. Vit. Horm. Fermentforsch.5, 51 (1952).

    Google Scholar 

  37. A. Zaffaroni, R. B. Burton, andE. H. Keutmann, Science111, 6 (1950); J. biol. Chem.188, 763 (1951);193, 749 (1951).

    Article  CAS  Google Scholar 

  38. I. E. Bush, Biochem. J.50, 370 (1952); Ciba Found. Colloquia on Endocrinol.5, 203 (1953);7, 210 (1953); J. Endocrinol.9, 95 (1953); J. biol. Chem.205, 783 (1953); Rec. Progr. Hormone Res.9, 321 (1954).

    Article  CAS  Google Scholar 

  39. V. Schwarz, Mem. Soc. Endocrinol.2, 75 (1953).

    Google Scholar 

  40. H. Schmidt andHj. Staudinger, Biochem. Z.324, 128 (1953).

    CAS  Google Scholar 

  41. K. Savard, J. biol. Chem.202, 457 (1953).

    Article  CAS  Google Scholar 

  42. R. Neher andA. Wettstein, Helv. chim. Acta34, 2278 (1951).

    Article  CAS  Google Scholar 

  43. M. Finkelstein, Nature169, 929 (1952).

    Article  CAS  Google Scholar 

  44. H. Reich, K. F. Crane, andS. J. Sanfilippo, J. organ. Chem.18, 822 (1953).

    Article  CAS  Google Scholar 

  45. A. G. Gornall andM. P. Macdonald, J. biol. Chem.201, 279 (1953).

    Article  CAS  Google Scholar 

  46. G. Zwingelstein, H. Pachéco, andJ. Jouanneteau, C. r. Acad. Sci, Paris236, 1561 (1953).

    CAS  Google Scholar 

  47. C. C. Porter andR. H. Silber, J. biol. Chem.185, 201 (1950)

    Article  CAS  Google Scholar 

  48. D. H. Nelson andL. T. Samuels, Rec. Prog. Hormone Res.9, 377 (1954); J. Clin. Endocrinol. Metabol.12, 519 (1952).

    Google Scholar 

  49. K. Eik-Nes, D. H. Nelson, andL. T. Samuels, J. Clin. Endocrinol. Metabol.13, 1280 (1953). Modification see:R. I. S. Bayliss andA. W. Steinbeck, Mem. Soc. Endocrinol.2, 31 (1953).

    Article  CAS  Google Scholar 

  50. V. Schwarz, Nature169, 506 (1952).

    Article  CAS  Google Scholar 

  51. A. A. Henley, Nature169, 877 (1952).

    Article  Google Scholar 

  52. H. E. Hadd andW. H. Perloff, Abstr. 126th Meeting Amer. Chem. Soc., 30C (1954).

  53. C. v. Holt, K. D. Voigt, andK. Gaede, Biochem. Z.323, 945 (1952).

    Google Scholar 

  54. K. D. Voigt andI. Beckmann, Acta Endocrinol.13, 19 (1953).

    CAS  Google Scholar 

  55. K. D. Voigt, W. Schroeder, I. Beckmann, andH. v. d. Werth, Acta Endocrinol.14, 1 (1953).

    CAS  Google Scholar 

  56. G. F. Marrian, J. Y. F. Paterson, andS. M. Atherden, Mem. Soc. Endocrinol.2, 4 (1953).G. F. Marrian, Rec. Progr. Hormone Res.9, 303 (1954).

    Google Scholar 

  57. R. W. H. Edwards andA. E. Kellie, Biochem. J.56, 207 (1954).

    Article  CAS  Google Scholar 

  58. L. R. Axelrod, J. Amer. chem. Soc.75, 4074 (1953).

    Article  CAS  Google Scholar 

  59. J. K. Norymberski, Nature170, 1074 (1952); Mem. Soc. Endocrinol.2, 50 (1953).

    Article  CAS  Google Scholar 

  60. J. K. Norymberski, J. Chem. Soc.1954, 762.

  61. H. Hübener, E. Hoffmann, andF. Bode, Z. physiol. Chemie289, 102 (1952).

    Article  Google Scholar 

  62. L. Dorfman, Chem. Rev.53, 47 (1953).

    Article  CAS  Google Scholar 

  63. S. Bernstein andR. H. Lenhard, J. org. Chem.18, 1146 (1953);19, 1269 (1954).

    Article  CAS  Google Scholar 

  64. R. N. Jones, P. Humphries, F. Herling, andK. Dobriner, J. Amer. chem. Soc.74, 2820 (1952).

    Article  CAS  Google Scholar 

  65. K. Dobriner, E. R. Katzenellenbogen, andR. N. Jones,Infrared Absorption Spectra of Steroids (New York, 1953).

  66. L. J. Bellamy, J. appl. Chem.3, 421 (1953).

    Article  CAS  Google Scholar 

  67. J. D. S. Goulden, Nature173, 646 (1954).

    Article  CAS  Google Scholar 

  68. J. K. N. Jones andS. R. Stitch, Biochem. J.53, 679 (1953).

    Article  CAS  Google Scholar 

  69. E. R. Katzenellenbogen, K. Dobriner, andTh. H. Kritchevsky, J. biol. Chem.207, 315 (1954).

    Article  CAS  Google Scholar 

  70. C. v. Holt, K. D. Voigt, andK. Gaede, Biochem. Z.323, 945 (1952).

    Google Scholar 

  71. K. D. Voigt andI. Beckmann, Acta Endocrinol.13, 19 (1953).

    CAS  Google Scholar 

  72. K. D. Voigt, W. Schroeder, I. Beckmann, andH. v. d. Werth, Acta Endocrinol.14, 1 (1953).

    CAS  Google Scholar 

  73. L. R. Axelrod andA. Zaffaroni, Arch. Biochem. Biophys.50, 347 (1954).

    Article  CAS  Google Scholar 

  74. R. I. Dorfman, Rec. Progr. Hormone Res.8, 87 (1953), Physiol. Rev.34, 152 (1954).

    Google Scholar 

  75. D. H. Nelson, Ciba Found. Colloquia Endocrinol.5, 162 (1953).

    Google Scholar 

  76. D. J. Ingle, Ciba Found. Colloquia Endocrinol.5, 175 (1953).

    Google Scholar 

  77. M. Vogt, Ciba Found. Colloquia Endocrinol.5, 186 (1953).

    Google Scholar 

  78. J. A. Nissim, Ciba Found. Colloquia Endocrinol.5, 193 (1953).

    Google Scholar 

  79. S. A. Simpson andJ. F. Tait, Endocrinology50, 150 (1952).

    Article  CAS  Google Scholar 

  80. C. M. Kagawa, E. G. Shipley, andR. K. Meyer, Proc. Soc. exper. Biol. Med.80, 281 (1952).

    Article  CAS  Google Scholar 

  81. P. Desaulles, J. Tripod, andW. Schuler, Schweiz. med. Wschr.83, 1088 (1953).

    CAS  Google Scholar 

  82. J. J. Pfiffner, W. W. Swingle, andH. M. Vars, J. biol. Chem.104, 701 (1934).

    Article  CAS  Google Scholar 

  83. F. Gross andR. Meier, Schweiz. med. Wschr.81, 1013 (1951).

    CAS  Google Scholar 

  84. J. F. Tait, S. A. Simpson, andH. M. Grundy, Lancet262, 122 (1952).

    Article  CAS  Google Scholar 

  85. H. M. Grundy, S. A. Simpson, J. F. Tait, andM. Woodford, Acta Endocrinol.11, 199 (1952).

    CAS  Google Scholar 

  86. S. A. Simpson, J. F. Tait, andI. E. Bush, Lancet263, 226 (1952).

    Article  CAS  Google Scholar 

  87. H. M. Grundy, S. A. Simpson, andJ. F. Tait, Nature169, 795 (1952).

    Article  CAS  Google Scholar 

  88. H. M. Grundy, S. A. Simpson, J. F. Tait, andM. Woodford, Acta Endocrinol.11, 199 (1952).

    CAS  Google Scholar 

  89. S. A. Simpson, andJ. F. Tait, Mem. Soc. Endocrinol.2, 9 (1953).

    Google Scholar 

  90. C. C. Porter andR. H. Silber, J. biol. Chem.185, 201 (1950).

    Article  CAS  Google Scholar 

  91. S. A. Simpson, J. F. Tait, A. Wettstein, R. Neher, J. v. Euw, andT. Reichstein, Exper.9, 333 (1953).

    CAS  Google Scholar 

  92. S. A. Simpson, J. F. Tait, A. Wettstein, R. Neher, J. v. Euw, O. Schindler, andT. Reichstein, Helv. chim. Acta37, 1163 (1954).

    Article  CAS  Google Scholar 

  93. I. E. Bush, Biochm. J.50, 370 (1952); Rec. Progr. Hormone Res.9, 453 (1954).

    Article  CAS  Google Scholar 

  94. A. Zaffaroni, R. B. Burton, andE. H. Keutmann, Science111, 6 (1950); J. biol. Chem.188, 763 (1951);193, 749 (1951).

    Article  CAS  Google Scholar 

  95. From the differences in the area of the spots in the lower and the upper series of these two systems shown in Figure 2, it followed that in this example aldosterone was contained primarily in fractions 46–49.

  96. I. E. Bush, Biochem. J.50, 370 (1952); Rec. Progr. Hormone Res.9, 453 (1954).

    Article  CAS  Google Scholar 

  97. R. Neher andA. Wettstein, Helv. chim. Acta34, 2278 (1951).

    Article  CAS  Google Scholar 

  98. H. M. Grundy, S. A. Simpson, J. F. Tait, andM. Woodford, Acta Endocrinol.11, 199 (1952).

    CAS  Google Scholar 

  99. S. A. Simpson andJ. F. Tait, Ciba Found. Colloqu. on Endocrinol.8 (1954), in press.

  100. R. Mattox, H. L. Mason, andA. Albert, Proc. Staff Meet. Mayo Clinic28, 569 (1953).

    CAS  Google Scholar 

  101. R. Mattox, H. L. Mason, A. Albert, andC. F. Code, J. Amer. chem. Soc.75, 4869 (1953).

    Article  CAS  Google Scholar 

  102. R. E. Knauff, E. D. Nielson, andW. J. Haines, J. Amer. chem. Soc.75, 4868 (1953).

    Article  CAS  Google Scholar 

  103. G. L. Farrell andJ. B. Richards, Fed. Proc.12, 41 (1953); Proc. Soc. exp. Biol. Med.83, 628 (1953);84, 89 (1953). According to a personal communication,Dr. Farrell and coworkers have made it highly probable that their product is essentially homogeneous and identical with aldosterone.

    Google Scholar 

  104. J. J. Majnarich andR. N. Dillon, Northwest Med.50, 677 (1951); Arch. Biochem. Biophys.49, 247 (1954).

    Google Scholar 

  105. K. D. Voigt andW. Schroeder, Naturwissenschaften40, 485 (1953).

    Article  CAS  Google Scholar 

  106. W. Schroeder, K. D. Voigt, andH. v. d. Werth, Acta Endocrinol.14, 12 (1953).

    CAS  Google Scholar 

  107. J. A. Luetscher, A. B. Deming, andB. B. Johnson, Ciba Found. Colloquia on Endocrinol.4, 530 (1952).

    Google Scholar 

  108. J. A. Luetscher andB. B. Johnson, Amer. J. Med.15, 417 (1953); J. clin. Invest.32, 585 (1953);33, 276 (1954). Other literature is given herein. See also: J. Clin. Endocrinol.14, 812, 1086 (1954). Test procedure compareB. B. Johnson, Endocrinology54, 196 (1954).

    Article  Google Scholar 

  109. B. Singer andE. H. Venning, Endocrinology52, 623 (1953).

    Article  CAS  Google Scholar 

  110. B. Singer andJ. Wener, Amer. Heart. J.45, 795 (1953);M. F. McCall andB. Singer, J. Clin. Endocrinol.13, 1157 (1953).

    Article  CAS  Google Scholar 

  111. Added when reading proofs: From a concentrate of this type, kindly made available to us by Dr.Luetscher, we9 were in fact able, by further chromatographic purification, to obtain considerable quantities of aldosterone in crystalline form. (Paper Exper. in press.)

  112. J. J. Chart andE. S. Shipley, J. clin. Invest.32, 560 (1953).

    Google Scholar 

  113. C. L. Cope andJ. Garcia, Brit. med. J.1954, 1290.

  114. E. S. Gordon, J. J. Chart, D. Hagedorn, andE. G. Shipley, Obstetr. and Gynecol.4, 39 (1954).

    CAS  Google Scholar 

  115. R. Neher andA. Wettstein, Unpublished data.

  116. S. A. Simpson, J. F. Tait, A. Wettstein, R. Neher, J. v. Euw, andT. Reichstein, Exper.9, 333 (1953).

    CAS  Google Scholar 

  117. S. A. Simpson, J. F. Tait, A. Wettstein, R. Neher, J. v. Euw, O. Schindler, andT. Reichstein, Helv. chim. Acta37, 1163 (1954).

    Article  CAS  Google Scholar 

  118. P. Desaulles, J. Tripod, andW. Schuler, Schweiz. med. Wschr.83, 1088 (1953); several papers on hormonal influences in water metabolism see Ciba Found. Colloquia on Endocrinol.4, 414 (1952).

    CAS  Google Scholar 

  119. E. Flückiger andF. Verzàr, Exper.10, 259 (1954).

    Google Scholar 

  120. F. Gross, Rec. Progr. Hormone Res.10 (in press).

  121. F. Gross andH. Gysel, Acta Endocrinol.15, 199 (1954).

    CAS  Google Scholar 

  122. W. W. Swingle, R. Maxwell, M. Ben, C. Baker, S. J. LeBrie, andM. Eisler, Proc. Soc. exper. Biol. Med.86, 147 (1954); Endocrinology54, 698 (1954); see also Endocrinology54 (1954), in press.

    Article  CAS  Google Scholar 

  123. R. E. Knauff, E. D. Nielson, andW. J. Haines, J. Amer. chem. Soc.75, 4868 (1953).

    Article  CAS  Google Scholar 

  124. W. Schuler, P. Desaulles, andR. Meier, Exper.10, 142 (1954).

    CAS  Google Scholar 

  125. R. Gaunt, A. S. Gordon, A. A. Renzi, J. Padawer, G. J. Fruhman, andM. Gilman, J. Clin. Endocrinol.14, 711 (1954); Endocrinology55, 236 (1954).

    Article  Google Scholar 

  126. R. S. Speirs, S. A. Simpson, andJ. F. Tait, Endocrinology55, 233 (1954).

    Article  CAS  Google Scholar 

  127. R. Gaunt, Ciba Found. Colloquia Endocrinol.8 (1954) (in press).

  128. A. A. Renzi, M. Gilman, andR. Gaunt, Proc. Soc. Exper. Biol. Med. (in press).

  129. S. A. Simpson andJ. F. Tait, Ciba Found. Colloqu. on Endocrinol.8 (1954), in press.

  130. R. S. Mach, J. Fabre, A. Duckert, R. Borth, andP. Ducommun, Schweiz. med. Wschr.84, 407 (1954).

    CAS  Google Scholar 

  131. L. Soffer, personal communication;G. W. Thorn, Colloquium onThe Human Adrenal Cortex II, The Ciba Foundation, London, June 1954.

  132. A. Kekwick andG. L. S. Pawan, Lancet267, 162 (1954).

    Article  CAS  Google Scholar 

  133. F. T. G. Prunty, R. R. McSwiney, andM. A. Smith, Lancet267 (1954), in press.

  134. S. A. Simpson, J. F. Tait, A. Wettstein, R. Neher, J. v. Euw, O. Schindler, andT. Reichstein, Exper.10, 132 (1954); Helv. chim. Acta37, 1200 (1954).

    CAS  Google Scholar 

  135. See e.g.S. Liebermann, B. Praetz, Ph. Humphries, andK. Dobriner, J. biol. Chem.204, 491 (1953).

    Article  Google Scholar 

  136. E. Vischer, J. Schmidlin, andA. Wettstein, Helv. chim. Acta37, 321 (1954).

    Article  Google Scholar 

  137. H. Hirschmann, F. B. Hirschmann, andG. L. Farrell, J. Amer. chem. Soc.75, 4862 (1953).

    Article  CAS  Google Scholar 

  138. W. Cole andP. L. Julian, J. org. Chem.19, 131 (1954).

    Article  CAS  Google Scholar 

  139. W. F. McGuckin, H. L. Mason, andG. M. Higgins, Abstr. 125th Meeting Amer. chem. Soc.1954, 4C.

  140. H. H. Inhoffen, F. Blomeyer, andK. Brückner, Ber. dtsch. chem. Ges.87, 593 (1954).

    Article  CAS  Google Scholar 

  141. K. Heusler andA. Wettstein, Chem. Ber.87, 1301, (1954).

    Article  CAS  Google Scholar 

  142. M. Hayano andR. I. Dorfman, Arch. Biochem. Biophys.50, 218 (1954).

    Article  CAS  Google Scholar 

  143. P. Th. Herzig andM. Ehrenstein, J. org. Chem.16, 1050 (1951).

    Article  CAS  Google Scholar 

  144. Ch. P. Balant andM. Ehrenstein, J. org. Chem.17, 1587 (1952).

    Article  CAS  Google Scholar 

  145. C. Amendolla, G. Rosenkranz, andF. Sondheimer, J. chem. Soc.1954, 1226; J. Amer. chem. Soc.75, 5930 (1953).

    Google Scholar 

  146. F. Sondheimer andG. Rosenkranz, Exper.9, 62 (1953).

    CAS  Google Scholar 

  147. K. Florey andM. Ehrenstein, J. org. Chem.19, 1331 (1954).

    Article  CAS  Google Scholar 

  148. F. Sondheimer, St. Kaufmann, J. Romo, H. Martinez, andG. Rosenkranz, J. Amer. chem. Soc.75, 4712 (1953).

    Article  CAS  Google Scholar 

  149. G. W. Barber andM. Ehrenstein, J. Amer. chem. Soc.76, 2026 (1954).

    Article  CAS  Google Scholar 

  150. P. Th. Herzig andM. Ehrenstein, J. org. Chem.17, 713 (1952).

    Article  CAS  Google Scholar 

  151. M. Ehrenstein, Chimia6, 287 (1952).

    Google Scholar 

  152. M. Ehrenstein, J. org. Chem.9, 435 (1944).

    Article  CAS  Google Scholar 

  153. G. W. Barber andM. Ehrenstein, J. org. Chem.19, 365 (1954).

    Article  CAS  Google Scholar 

  154. A. Sandoval, L. Miramontes, G. Rosenkranz, C. Djerassi, andF. Sondheimer, J. Amer. chem. Soc.75, 4117 (1953).

    Article  CAS  Google Scholar 

  155. C. Djerassi, L. Miramontes, andG. Rosenkranz, J. Amer. chem. Soc.75, 4440 (1953).

    Article  CAS  Google Scholar 

  156. F. W. Kahnt, Ch. Meystre, R. Neher, E. Vischer, andA. Wettstein, Exper.8, 422 (1952).

    CAS  Google Scholar 

  157. S. H. Eppstein, P. D. Meister, D. H. Peterson, H. C. Murray, H. M. Leigh, D. A. Lyttle, L. M. Reineke, andA. Weintraub, J. Amer. chem. Soc.75, 408 (1953).

    Article  CAS  Google Scholar 

  158. J. Fried, R. W. Thoma, J. R. Gerke, J. E. Herz, M. N. Donin, andD. Perlman, J. Amer. chem. Soc.74, 3962 (1952).

    Article  CAS  Google Scholar 

  159. D. H. Peterson, S. H. Eppstein, P. D. Meister, B. J. Magerlein, H. C. Murray, H. M. Leigh, A. Weintraub, andL. M. Reineke, J. Amer. chem. Soc.75, 412 (1953).

    Article  CAS  Google Scholar 

  160. W. J. Adams, B. G. Cross, A. David, F. Hartley, D. Patel, V. Petrow, andI. A. Stuart, J. Pharmacy Pharmacol. (Brit.)5, 861 (1953).

    Article  CAS  Google Scholar 

  161. R. Casanova, C. W. Shoppee, andG. H. R. Summers, J. chem. Soc.1953, 2983.

  162. R. Casanova, A. Ruff, andC. W. Shoppee, Ciba Found. Colloquia on Endocrinol.7, 59 (1953).

    Google Scholar 

  163. J. Fried andE. F. Sabo, J. Amer. chem. Soc.75, 2273 (1953).

    Article  CAS  Google Scholar 

  164. R. P. Graber, A. C. Haven, andN. L. Wendler, J. Amer. chem. Soc.75, 4722 (1953).

    Article  CAS  Google Scholar 

  165. S. Bernstein, R. Littell, andJ. H. Williams, J. Amer. chem. Soc.75, 4830 (1953).

    Article  CAS  Google Scholar 

  166. Merck Institute for Therapeutic Research. Personal communication from Dr.N. L. Wendler.

  167. J. Fried andE. F. Sabo, J. Amer. chem. Soc.76, 1455 (1954).

    Article  CAS  Google Scholar 

  168. A. Borman andF. M. Singer, Fed. Proc.13, 185 (1954).

    Google Scholar 

  169. A. Borman, F. M. Singer, andP. Numerof, Proc. Soc. Exper. Biol. Med.86, 570 (1954).

    Article  CAS  Google Scholar 

  170. See also:G. W. Liddle, M. M. Pechet, andF. C. Bartter, J. Clin. Endocrinol.14, 813 (1954).

    Article  Google Scholar 

  171. G. W. Thorn, Colloquium onThe Human Adrenal Cortex II, The Ciba Foundation, London, June, 1954.

    Google Scholar 

  172. E. F. Rogers, W. J. Leanza, J. P. Conbere, and K. Pfister, J. Amer. chem. Soc.74, 2947 (1952);76, 1691 (1954).

    Article  CAS  Google Scholar 

  173. J. J. Schneider, J. Amer. chem. Soc.75, 2024 (1953).

    Article  CAS  Google Scholar 

  174. T. H. Kritchevsky, D. L. Garmaise, andT. F. Gallagher, J. Amer. chem. Soc.74, 483 (1952).

    Article  CAS  Google Scholar 

  175. St. Kaufmann andJ. Pataki, Exper.7, 260 (1951).

    CAS  Google Scholar 

  176. E. Wilson andM. Tishler, J. Amer. chem. Soc.74, 1609 (1952).

    Article  CAS  Google Scholar 

  177. E. P. Oliveto, C. Gerold, andE. B. Hershberg, J. Amer. chem. Soc.74, 2248 (1952).

    Article  CAS  Google Scholar 

  178. V. R. Mattox andE. C. Kendall, J. biol. Chem.188, 287 (1951).

    Article  CAS  Google Scholar 

  179. V. R. Mattox, E. L. Woroch, G. A. Fleisher, andE. C. Kendall, J. biol. Chem.197, 261 (1952).

    Article  CAS  Google Scholar 

  180. G. M. Higgins, K. A. Woods, andE. C. Kendall, Endocrinology48, 175 (1951).

    Article  CAS  Google Scholar 

  181. R. M. Dodson, P. B. Sollman, andB. Riegel, J. Amer. chem. Soc.75, 5132 (1953).

    Article  CAS  Google Scholar 

  182. Ch. R. Engel andG. Just, J. Amer. chem. Soc.76 (1954) in press.

  183. H. Heusser, private communication.

  184. J. Heer andA. Wettstein, Helv. chim. Acta36, 891 (1953).

    Article  CAS  Google Scholar 

  185. M. E. Herr andF. W. Heyl, J. Amer. chem. Soc.72, 2617 (1950);74, 3627 (1952).

    Article  Google Scholar 

  186. A. F. B. Cameron, J. S. Hunt, J. F. Oughton, P. A. Wilkinson, andB. M. Wilson, J. chem. Soc.1953, 3864.

  187. F. Reber, A. Lardon, andT. Reichstein, Helv. chim. Acta37, 45 (1954).

    Article  CAS  Google Scholar 

  188. A. Lardon andT. Reichstein, Helv. chim. Acta37, 388, 443 (1954).

    Article  CAS  Google Scholar 

  189. L. H. Sarett, G. E. Arth, R. M. Lukas, R. E. Beyler, G. I. Poos, W. F. Johns, andJ. M. Constantin, J. Amer. chem. Soc.74, 4974 (1952).

    Article  CAS  Google Scholar 

  190. A. Ercoli andP. de Ruggieri, Gazz. chim. ital.84, 312 (1954).

    CAS  Google Scholar 

  191. R. B. Moffett andD. I. Weisblat, J. Amer. chem. Soc.74, 2183 (1952).

    Article  CAS  Google Scholar 

  192. C. Djerassi andC. T. Lenk, J. Amer. chem. Soc.75, 3493 (1953);76, 1722 (1954).

    Article  CAS  Google Scholar 

  193. According toGallagher* the latter are also obtained from the 20, 21-enol-acetates XXXVI with perbenzoic acid and silica gel under rearrangement.

  194. H. Vanderhaeghe, E. R. Katzenellenbogen, K. Dobriner, andT. F. Gallagher, J. Amer. chem. Soc.74, 2810 (1952).

    Article  CAS  Google Scholar 

  195. A. H. Soloway, W. J. Considine, K. D. Fukushima, andT. F. Gallagher, J. Amer. chem. Soc.76, 2941 (1954).

    Article  CAS  Google Scholar 

  196. Compare also:F. B. Colton, W. R. Nes, D. A. van Dorp, H. L. Mason, andE. C. Kendall, J. biol. Chem.194, 235 (1952).

    Article  CAS  Google Scholar 

  197. F. B. Colton andE. C. Kendall, J. biol. Chem.194, 247 (1952).

    Article  CAS  Google Scholar 

  198. H. V. Anderson, E. R. Garrett, F. H. Lincoln, A. H. Nathan, andJ. A. Hogg, J. Amer. chem. Soc.76, 743 (1954).

    Article  CAS  Google Scholar 

  199. D. H. R. Barton, R. M. Evans, J. C. Hamlet, P. G. Jones, andT. Walker, J. Chem. Soc.1954, 747.

  200. R. B. Moffett andH. V. Anderson, J. Amer. chem. Soc.76, 747 (1954) and literature cited therein.

    Article  CAS  Google Scholar 

  201. J. Schmidlin andA. Wettstein, Helv. chim. Acta36, 1241 (1953).

    Article  CAS  Google Scholar 

  202. J. W. Cornforth andJ. M. Osbond, Chem. and Ind.1953, 919.

  203. J. W. Cornforth, J. M. Osbond, andG. H. Philipps, J. chem. Soc.1954, 907.

  204. CompareG. P. Mueller andL. L. Norton, J. Amer. chem. Soc.76, 749 (1954).

    Article  CAS  Google Scholar 

  205. CompareA. Fürst andR. Scotoni, Helv. chim. Acta36, 1410 (1953).

    Article  Google Scholar 

  206. N. L. Wendler, R. B. Graber, R. E. Jones, andM. Tishler, J. Amer. chem. Soc.72, 5793 (1950);74, 3630 (1952).

    Article  CAS  Google Scholar 

  207. N. L. Wendler, Huang-Minlon, andM. Tishler, J. Amer. chem. Soc.73, 3818 (1951).

    Article  CAS  Google Scholar 

  208. R. Antonucci, S. Bernstein, M. Heller, R. Lenhard, R. Littell, andJ. H. Williams, J. org. Chem.18, 70 (1953);

    Article  CAS  Google Scholar 

  209. see alsoR. Antonucci, S. Bernstein, andR. Lenhard, J. Amer. chem. Soc.76, 2956 (1954),

    Article  CAS  Google Scholar 

  210. furthermoreR. H. Levin, B. J. Magerlein, A. V. McIntosh, A. R. Hanze, G. S. Fonken, J. L. Thompson, A. M. Searcy, A. M. Scheri, andE. S. Gutsell, J. Amer. chem. Soc.75, 502 (1953);76, 546 (1954).

    Article  CAS  Google Scholar 

  211. A. R. Hanze, G. S. Fonken, A. V. McIntosh, A. M. Searcy, andR. H. Levin, J. Amer. chem. Soc.76, 3179 (1954).

    Article  CAS  Google Scholar 

  212. E. P. Oliveto, T. Clayton, andE. B. Hershberg, J. Amer. chem. Soc.75, 486 (1953).

    Article  CAS  Google Scholar 

  213. O. Mancera, A. Zaffaroni, B. A. Rubin, F. Sondheimer, G. Rosenkranz, andC. Djerassi, J. Amer. chem. Soc.74, 3711 (1952).

    Article  CAS  Google Scholar 

  214. A. H. Soloway, A. S. Deutsch, andT. F. Gallagher, J. Amer. chem. Soc.75, 2356 (1953).

    Article  CAS  Google Scholar 

  215. J. K. Norymberski andG. F. Woods, Chem. and Ind.1954, 518.

  216. H. Heusser, R. Anliker, andO. Jeger, Helv. chim. Acta35, 1537 (1952).

    Article  CAS  Google Scholar 

  217. F. Sondheimer, R. Yashin, G. Rosenkranz, andC. Djerassi, J. Amer. chem. Soc.74, 2696 (1952).

    Article  CAS  Google Scholar 

  218. H. L. Herzog, E. P. Oliveto, M. A. Jevnik, andE. B. Hershberg, J. Amer. chem. Soc.74, 4470 (1952).

    Article  CAS  Google Scholar 

  219. S. Bernstein, R. Littell, andJ. H. Williams, J. Amer. chem. Soc.75, 1481 (1953).

    Article  CAS  Google Scholar 

  220. E. P. Oliveto, H. L. Herzog, andE. B. Hershberg, J. Amer. chem. Soc.75, 1505 (1953).

    Article  CAS  Google Scholar 

  221. J. M. Constantin, A. C. Haven, andL. H. Saertt, J. Amer. chem. Soc.75, 1716 (1953).

    Article  CAS  Google Scholar 

  222. H. J. Dauben, B. Löken, andH. J. Ringold, J. Amer. chem. Soc.76, 1359 (1954).

    Article  CAS  Google Scholar 

  223. C. Djerassi andM. Gorman, J. Amer. chem. Soc.75, 3704 (1953).

    Article  CAS  Google Scholar 

  224. L. F. Fieser, J. Amer. chem. Soc.76, 1945 (1954).

    Article  CAS  Google Scholar 

  225. M. E. Herr andF. W. Heyl, J. Amer. chem. Soc.74, 3627 (1952);75, 1918, 5927 (1953).

    Article  CAS  Google Scholar 

  226. G. Rosenkranz andF. Sondheimer, Progr. Chem. Org. Natur. Prod.10, 274 (1953.

    CAS  Google Scholar 

  227. Compare however:H. Heusser andO. Jeger, Ciba Found. Colloquia on Endocrinol.7, 46 (1953).

    Google Scholar 

  228. C. Djerassi andG. Rosenkranz, Ciba Found. Colloquia on Endocrinol.7, 79 (1953).

    Google Scholar 

  229. F. S. Spring et al., Ciba Found. Colloquia on Endocrinol.7, 96 (1953).

    Google Scholar 

  230. G. Rosenkranz et al., Rec. Progr. Hormone Res.8, 1 (1953).

    Google Scholar 

  231. H. B. Henbest andE. R. H. Jones, Ciba Found. Colloquia on Endocrinol.7, 39 (1953).

    Google Scholar 

  232. H. H. Inhoffen andW. Mengel, Chem. Ber.87, 146 (1954).

    Article  CAS  Google Scholar 

  233. A. Zürcher, H. Heusser, O. Jeger, andP. Geistlich, Helv. chim. Acta37, 1562 (1954).

    Article  Google Scholar 

  234. P. Bladon, H. B. Henbest, E. R. H. Jones, B. J. Lovell, andG. F. Woods, J. chem. Soc.1954, 125, and literature cited therein.

  235. K. Heusler andA. Wettstein, Helv. chim. Acta36, 398 (1953).

    Article  CAS  Google Scholar 

  236. E. Schoenewaldt, L. Turnbull, E. M. Chamberlin, D. Reinhold, A. E. Erickson, W. V. Ruyle, J. M. Chemerda, andM. Tishler, J. Amer. chem. Soc.74, 2696 (1952).

    Article  CAS  Google Scholar 

  237. F. Sondheimer, R. Yashin, G. Rosenkranz, andC. Djerassi, J. Amer. chem. Soc.74, 2696 (1952).

    Article  CAS  Google Scholar 

  238. CompareC. Djerassi, W. Frick, G. Rosenkranz, andF. Sondheimer, J. Amer. chem. Soc.75, 3496 (1953).

    Article  CAS  Google Scholar 

  239. M. E. Herr andF. W. Heyl, J. Amer. chem. Soc.72, 2617 (1950);74, 3627 (1952).

    Article  Google Scholar 

  240. A. F. B. Cameron, J. S. Hunt, J. F. Oughton, P. A. Wilkinson, andB. M. Wilson, J. chem. Soc.1953, 3864.

  241. D. Maclean, W. S. Strachan, andF. S. Spring, Chem. and Ind.1953, 1259.

  242. R. O. Stafford, L. C. Thole, andK. J. Olson, Endocrinology52, 292 (1953).

    Article  CAS  Google Scholar 

  243. Reviews:D. H. Peterson, Research6, 309 (1953).

    CAS  Google Scholar 

  244. K. Florey, Chimia8, 81 (1954).

    CAS  Google Scholar 

  245. R. I. Dorfman andF. Ungar,Metabolism of Steroid Hormones (Minneapolis, 1953).

  246. F. Johnson, G. T. Newbold, andF. S. Spring, J. chem. Soc.1954, 1302.

  247. D. H. Peterson andH. C. Murray, J. Amer. chem. Soc.74, 1871 (1952).

    Article  CAS  Google Scholar 

  248. F. W. Kahnt, Ch. Meystre, R. Neher, E. Vischer, andA. Wettstein, Exper.8, 422 (1952).

    CAS  Google Scholar 

  249. A. Wettstein, inL. Weissbecker,Probleme des Hypophysen-Nebennierenrindensystems (Berlin, 1953), p. 33.

  250. O. Mancera, A. Zaffaroni, B. A. Rubin, F. Sondheimer, G. Rosenkranz, andC. Djerassi, J. Amer. chem. Soc.74, 3711 (1952).

    Article  CAS  Google Scholar 

  251. D. H. Peterson, H. C. Murray, S. H. Eppstein, L. M. Reineke, A. Weintraub, P. D. Meister, andH. M. Leigh, J. Amer. chem. Soc.74, 5933 (1952).

    Article  CAS  Google Scholar 

  252. J. Fried, R. W. Thoma, J. R. Gerke, J. E. Herz, M. N. Donin, andD. Perlman, J. Amer. chem. Soc.74, 3962 (1952).

    Article  CAS  Google Scholar 

  253. S. H. Eppstein, P. D. Meister, D. H. Peterson, H. C. Murray, H. M. Leigh, D. A. Lyttle, L. M. Reineke, andA. Weintraub, J. Amer. chem. Soc.75, 408 (1953).

    Article  CAS  Google Scholar 

  254. D. H. Peterson, S. H. Eppstein, P. D. Meister, B. J. Magerlein, H. C. Murray, H. M. Leigh, A. Weintraub, andL. M. Reineke, J. Amer. chem. Soc.75, 412 (1953).

    Article  CAS  Google Scholar 

  255. P. D. Meister, D. H. Peterson, H. C. Murray, G. B. Spero, S. H. Eppstein, A. Weintraub, L. M. Reineke, andH. M. Leigh, J. Amer. chem. Soc.75, 416 (1953).

    Article  CAS  Google Scholar 

  256. D. H. Peterson, A. H. Nathan, P. D. Meister, S. H. Eppstein, H. C. Murray, A. Weintraub, L. M. Reineke, andH. M. Leigh, J. Amer. chem. Soc.75, 419 (1953).

    Article  CAS  Google Scholar 

  257. S. H. Eppstein, H. D. Peterson, H. M. Leigh, H. C. Murray, A. Weintraub, L. M. Reineke, andP. D. Meister, J. Amer. chem. Soc.75, 421 (1953).

    Article  CAS  Google Scholar 

  258. P. D. Meister, D. H. Peterson, H. C. Murray, S. H. Eppstein, L. M. Reineke, A. Weintraub, andH. M. Leigh, J. Amer. chem. Soc.75, 55 (1953).

    Article  CAS  Google Scholar 

  259. F. W. Kahnt, Ch. Meystre, R. Neher, E. Vischer, andA. Wettstein, Exper.8, 422 (1952).

    CAS  Google Scholar 

  260. O. Mancera, A. Zaffaroni, B. A. Rubin, F. Sondheimer, G. Rosenkranz, andC. Djerassi, J. Amer. chem. Soc.74, 3711 (1952).

    Article  CAS  Google Scholar 

  261. A. H. Soloway, A. S. Deutsch, andT. F. Gallagher, J. Amer. chem. Soc.75, 2356 (1953).

    Article  CAS  Google Scholar 

  262. O. Mancera, H. J. Ringold, C. Djerassi, G. Rosenkranz, andF. Sondheimer, J. Amer. chem. Soc.75, 1286 (1953).

    Article  CAS  Google Scholar 

  263. R. H. Levin, B. J. Magerlein, A. V. McIntosh, A. R. Hanze, G. S. Fonken, J. L. Thompson, A. M. Searcy, M. A. Scheri, andE. S. Gutsell, J. Amer. chem. Soc.75, 502 (1953);76, 546 (1954).

    Article  CAS  Google Scholar 

  264. A. R. Hanze, G. S. Fonken, A. V. McIntosh, A. M. Searcy, andR. H. Levin, J. Amer. chem. Soc.76, 3179 (1954).

    Article  CAS  Google Scholar 

  265. J. Fried andE. F. Sabo, J. Amer. chem. Soc.75, 2273 (1953).

    Article  CAS  Google Scholar 

  266. Chemical syntheses see:J. Romo, G. Rosenkranz, C. Djerassi, andF. Sondheimer, J. Amer. chem. Soc.75, 1277 (1953).

    Article  CAS  Google Scholar 

  267. E. P. Oliveto, H. L. Herzog, M. A. Jevnik, H. E. Jorgensen, andE. B. Hershberg, J. Amer. chem. Soc.75, 3651 (1953).

    Article  CAS  Google Scholar 

  268. D. R. Colingsworth, J. N. Karnemaat, F. R. Hanson, M. P. Brunner, K. M. Mann, andW. J. Haines, J. biol. Chem.203, 807 (1953).

    Article  CAS  Google Scholar 

  269. F. R. Hanson, K. M. Mann, E. D. Nielson, H. V. Anderson, M. P. Brunner, J. N. Karnemaat, D. R. Colingsworth, andW. J. Haines, J. Amer. chem. Soc.75, 5369 (1953).

    Article  CAS  Google Scholar 

  270. G. M. Shull, R. Heights, D. A. Kita, J. Heights, andJ. W. Davisson, US. Pat. 2658023 (1953).

  271. H. C. Murray andD. H. Peterson, US. Pat. 2602769 (1952).

  272. P. D. Meister et al., Abstr. 123rd Meet. Amer. chem. Soc.1953, 5C.

  273. E. Vischer, J. Schmidlin, andA. Wettstein, Helv. chim. Acta37, 321 (1954.

    Article  Google Scholar 

  274. D. Perlman, E. Titus, andJ. Fried, J. Amer. chem. Soc.74, 2126 (1952).

    Article  CAS  Google Scholar 

  275. Ch. Meystre, E. Vischer, andA. Wettstein, Helv. chim. Acta37, 1548 (1954). Added when reading the proofs: In the meantime alsoP. D. Meister et al. (J. Amer. Soc.76, 4050 (1954) described the microbiological introduction of the 17α-hydroxyl group.

    Article  CAS  Google Scholar 

  276. J. E. Plager andL. T. Samuels, Feder. Proc.12, 357 (1953); Arch. Biochem. Biophys.42, 477 (1953); J. biol. Chem. 1954, (in press).

    Google Scholar 

  277. R. H. Levin, B. J. Magerlein, A. V. McIntosh, A. R. Hanze, G. S. Fonken, J. L. Thompson, A. M. Searcy, M. A. Scheri andE. S. Gutsell, J. Amer. chem. Soc.75, 502 (1953);76, 546 (1954).

    Article  CAS  Google Scholar 

  278. A. R. Hanze, G. S. Fonken, A. V. McIntosh, A. M. Searcy, andR. H. Levin, J. Amer. chem Soc.76, 3179 (1954).

    Article  CAS  Google Scholar 

  279. C. Amendolla, G. Rosenkranz, andF. Sondheimer, J. chem. Soc.1954, 1226; J. Amer. chem. Soc.75, 5930 (1953).

    Google Scholar 

  280. F. Sondheimer andG. Rosenkranz, Exper.9, 62 (1953).

    CAS  Google Scholar 

  281. H. B. Henbest andE. R. Jones, Ciba Found. Colloquia on Endocrinol.7, 39 (1953).

    Google Scholar 

  282. H. H. Inhoffen &W. Mengel, Chem. Ber.87, 146 (1954).

    Article  CAS  Google Scholar 

  283. A. Zurcher, H. Heusser, O. Jeger &P. Geistlich, Helv.37, 1562 (1954).

    Article  CAS  Google Scholar 

  284. P. Bladon, H. B. Henbest, E. R. H. Jones, B. J. Lovell, &G. F. Woods, J. Chem. Soc.1954, 125, and literature cited therein.

  285. F. Reber, A. Lardon, andT. Reichstein, Helv. chim. Acta37, 45 (1954).

    Article  CAS  Google Scholar 

  286. A. Lardon andT. Reichstein, Helv. chim. Acta37, 388, 443 (1954).

    Article  CAS  Google Scholar 

  287. E. P. Oliveto, C. Gerold, andE. B. Hershberg, Arch. Biochem. Biophys.49, 244 (1954).

    Article  CAS  Google Scholar 

  288. Huang-Minlon, E. Wilson, N. L. Wendler, andM. Tishler, J. Amer. chem. Soc.74, 5394 (1952).

    Article  CAS  Google Scholar 

  289. R. B. Turner, J. Amer. chem. Soc.75, 3489 (1953).

    Article  CAS  Google Scholar 

  290. E. P. Oliveto, C. Gerold, andE. B. Hershberg, J. Amer. chem. Soc.43, 234 (1953).

    CAS  Google Scholar 

  291. E. P. Oliveto, C. Gerold, L. Weber, H. E. Jorgensen, R. Rausser, andE. B. Hershberg, J. Amer. chem. Soc.75, 5486 (1953).

    Article  CAS  Google Scholar 

  292. P. Wieland, J. Heer, J. Schmidlin, andK. Miescher, Helv. chim. Acta34, 354 (1951).

    Article  CAS  Google Scholar 

  293. F. Gross andE. Tschopp, Exper.8, 75 (1952).

    CAS  Google Scholar 

  294. P. Desaulles andR. Meier, Schweiz. med. Wschr.84, 741 (1954).

    CAS  Google Scholar 

  295. Review see:C. A. Finch, Manufacturing Chemist24, 509 (1953).

    CAS  Google Scholar 

  296. A. R. Pinder andR. Robinson, Nature167, 484 (1951).

    Article  CAS  Google Scholar 

  297. H. M. E. Cardwell, J. W. Cornforth, S. R. Duff, H. Holtermann, andR. Robinson, Chem. and Ind.1951, 389; J. chem. Soc.1953, 361.

  298. R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, andW. M. McLamore, J. Amer. chem. Soc.73, 2403 (1951);74, 4223 (1952).

    Article  CAS  Google Scholar 

  299. R. B. Woodward, F. Sondheimer, andD. Taub, J. Amer. chem. Soc.73, 3547, 3548, 4057 (1951); Ref. in Chemical Age69, 1222 (1953).

    Article  CAS  Google Scholar 

  300. B. Barkley, M. W. Farrar, W. S. Knowles, andH. Raffelson, J. Amer. chem. Soc.75, 4110 (1953).

    Article  CAS  Google Scholar 

  301. L. H. Sarett, R. M. Lukes, G. I. Poos, J. M. Robinson, R. E. Beyler, J. M. Vandegrift, andG. E. Arth, J. Amer. chem. Soc.74, 1393 (1952).

    Article  CAS  Google Scholar 

  302. R. E. Beyler andL. H. Sarett, J. Amer. chem. Soc.74, 1397, 1406 (1952).

    Article  CAS  Google Scholar 

  303. R. M. Lukes, G. I. Poos andL. H. Sarett, J. Amer. chem. Soc.74, 1401 (1952).

    Article  CAS  Google Scholar 

  304. L. H. Sarett, G. E. Arth, R. M. Lukes, R. E. Beyler, G. I. Poos, W. F. Johns, andJ. M. Constantin, J. Amer. chem. Soc.74, 4974 (1952).

    Article  CAS  Google Scholar 

  305. G. I. Poos, G. E. Arth, R. E. Beyler, andL. H. Sarett, J. Amer. chem. Soc.75, 422 (1953).

    Article  CAS  Google Scholar 

  306. R. M. Lukes, G. I. Poos, R. E. Beyler, W. F. Johns, andL. H. Sarett, J. Amer. chem. Soc.75, 1707 (1953).

    Article  CAS  Google Scholar 

  307. L. H. Sarett, W. F. Johns, R. E. Beyler, R. M. Lukes, G. I. Poos, andG. E. Arth, J. Amer. chem. Soc.75, 2112 (1953).

    Article  CAS  Google Scholar 

  308. G. E. Arth, G. I. Poos, R. M. Lukes, F. M. Robinson, W. F. Johns, M. Feurer, andL. H. Sarett, J. Amer. chem. Soc.76, 1715 (1954).

    Article  CAS  Google Scholar 

  309. R. M. Lukes andL. H. Sarett, J. Amer. chem. Soc.76, 1178 (1954).

    Article  CAS  Google Scholar 

  310. W. S. Johnson, B. Bannister, B. M. Bloom, A. D. Kemp, R. Pappo, E. R. Rogier, andJ. Szmuszkovicz, J. Amer. chem. Soc.75, 2275 (1953).

    Article  CAS  Google Scholar 

  311. W. S. Johnson, R. Pappo, andA. D. Kemp, J. Amer. chem Soc.76, 3353 (1954).

    Article  CAS  Google Scholar 

  312. P. Wieland, H. Überwasser, G. Anner, andK. Miescher, Helv. chim. Acta36, 1231 (1953).

    Article  CAS  Google Scholar 

  313. A. L. Wilds, J. W. Ralls, W. C. Wildman, andK. E. McCaleb, J. Amer. chem. Soc.75, 5794 (1950).

    Article  Google Scholar 

  314. A. L. Wilds, J. W. Ralls, D. A. Tyner, R. Daniels, St. Kraychy, andM. Harnik, J. Amer. chem. Soc.75, 4878 (1953).

    Article  CAS  Google Scholar 

  315. Review see:O. Hechter andG. Pincus, Physiol. Rev.34, 459 (1954).

    Article  CAS  Google Scholar 

  316. Compare e.g.:M. Gut, Helv. chim. Acta36, 906 (1953).

    Article  CAS  Google Scholar 

  317. G. I. Fujimoto andJ. Prager, J. Amer. chem Soc.75, 3259 (1953).

    Article  CAS  Google Scholar 

  318. L. M. Thompson, C. H. Yates, andA. D. Odell, J. Amer. chem Soc.76, 1194 (1954).

    Article  CAS  Google Scholar 

  319. E. Schwenk, N. T. Werthessen andA. F. Colton, Arch. Biochem. Biophys.48, 322 (1954).

    Article  CAS  Google Scholar 

  320. R. D. H. Heard et al., Rec. Progr. Hormone Res.9, 383 (1954).

    Google Scholar 

  321. T. F. Gallagher et al., Rec. Progr. Hormone Res.9, 411 (1954).

    Google Scholar 

  322. M. L. Sweat, J. Amer. chem. Soc.73, 4056 (1951).

    Article  CAS  Google Scholar 

  323. M. Hayano andR. I. Dorfman, Feder. Proc.11, 228 (1952); J. biol. Chem.200, 175 (1953).

    Google Scholar 

  324. J. E. Plager andL. T. Samuels, Feder. Proc.11, 383 (1952);12, 357 (1953); Arch. Biochem. Biophys.42, 477 (1953); J. biol. Chem. (1954) in press.

    Google Scholar 

  325. L. T. Samuels,Endocrinological Symposium, Marburg, June 1954.

  326. O. Hechter, Ciba Found. Colloquia on Endocrinol.7, 204 (1953).

    Google Scholar 

  327. Dorfman now observes a certain degree of 21-hydroxylation in 21-desoxycortisone by adrenal homogenates (Discussion subsequent to5).

  328. A. Wettstein, F. W. Kahnt, andR. Neher, Ciba Foundation Colloquia on Endocrinol.8 (1954), in press; compare literature cited therein.

  329. W. J. Haines, Rec. Progr. Hormone Res.7, 255 (1952).

    Google Scholar 

  330. F. W. Kahnt andA. Wettstein, Helv. chim. Acta34, 1790 (1951).

    Article  CAS  Google Scholar 

  331. F. W. Kahnt, Ch. Meystre, R. Neher, E. Vischer, andA. Wettstein, Exper.8, 422 (1952).

    CAS  Google Scholar 

  332. A. C. Brownie andJ. K. Grant, Biochem. J.57, 255 (1954).

    Article  CAS  Google Scholar 

  333. A. Wettstein, F. W. Kahnt, andR. Neher, Ciba Foundation Colloquia on Endocrinol.8 (1954), in press.

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Authors and Affiliations

  1. Research Department, Ciba Ltd., Basle

    A. Wettstein & G. Anner

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  1. A. Wettstein
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  2. G. Anner
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Based on a talk at the Gordon Research Conference on the Chemistry of Steroids, organized by the American Association for the Advancement of Science, New Hampton N.H., August 4, 1954. Communication No. 125 “On Steroids”. No. 124 compareK. Heusler andA. Wettstein, Chem. Ber.87, 1301, 1954.

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Wettstein, A., Anner, G. Advances in the field of adrenal cortical hormones. Experientia 10, 397–416 (1954). https://doi.org/10.1007/BF02318502

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