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The Dolastatins

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Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products

Abstract

Certain marine animals were known to the ancients for their potent biological constituents and presumed use in primitive medicine. The early periods of recorded history contain references to support these assumptions (1). Illustrative are hieroglyphics on the Egyptian Pharaoh Ti’s tomb (approximately 2700 BC) that describe the poisonous puffer fish Tetraodon stellatus. One of the earliest recorded uses of a marine organism in primitive medical practice has been attributed to the Roman, Gaius Plinius Secundus (AD 29–79, Pliny the Elder), who recommended that the sting system of the stingray be ground up and used for treatment of toothache and in obstetrics. One of the first modern pharmacological and chemical studies of potent marine animal constituents involved tetrodotoxin from the poisonous puffer fish (2, 3). About 40 years ago some especially important observations began to be recorded. Illustrative was the fact that extracts from certain sponges and coelenterates were shown to have antibiotic properties (4–8) and that marine invertebrates produce various other potentially medically useful components (9–11). Very importantly, from the viewpoint of anticancer drug discovery, were reports that starfish meal (12–14) and fractions from the peanut worm Bonellia fulginosa (15, 16), certain sea cucumbers, and molluscs [clams (16) and oysters (9, 11)] exhibited antitumor activity against sarcoma-180 and Krebs-2 ascites tumor (10, 17–19).

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References

  1. Halstead, B.W.: Poisonous and Venomous Marine Animals of the World, Vols. 1, 2. Washington, D.C.: US Government Printing Office. 1965, 1967.

    Google Scholar 

  2. Woodward, R.B., and J.Z. Gougoutas: The Structure of Tetrodotoxin. J. Amer. Chem. Soc., 86, 5030 (1964).

    CAS  Google Scholar 

  3. Goto, T., Y. Kishi, S. Takahashi, and Y. Hirata: Tetrodotoxin. Tetrahedron, 21, 2059 (1965).

    CAS  Google Scholar 

  4. Nigrelli, R.F., S. Jakowska, and I. Calventi: Ectyonin, an Antimicrobial Agent from the Sponge Microciona prolifera Verrill. Zoologica, 44, 173 (1959).

    CAS  Google Scholar 

  5. Jakowska, S., and R.F. Nigrelli: Antimicrobial Substances from Sponges. Ann. NY Acad. Sci., 90, 913(1960).

    CAS  Google Scholar 

  6. Burkholder, P.R., and L.M. Burkholder: Antimicrobial Activity of Horny Corals. Science, 127, 1174(1958).

    CAS  Google Scholar 

  7. Ciereszko, L.S., D.H. Sifford, and A.J. Weinheimer: Chemistry of Coelenterates. I. Occurrence of Terpenoid Compounds in Gorgonians. Ann. NY Acad. Sci., 90, 917 ( 1960).

    Google Scholar 

  8. Ciereszko, L.S.: Chemistry of Coelenterates, III: Occurrence of Antimicrobial Terpenoid Compounds in the Zooxanthellae of Alcyonarians. Trans. NY Acad. Sci., 24, 502 (1962).

    CAS  Google Scholar 

  9. Marderosian, A.H.D.: Marine Pharmaceuticals. J. Pharm. Sci., 58, 1 (1969).

    CAS  Google Scholar 

  10. Nigrelli, R.F., M.F. Stempien, C.D. Ruggieri, V.R. Ligouri, and J.T. Cecil: Substances of Potential Biomedical Importance from Marine Organisms. Fed. Proa, 26, 1197 (1967).

    CAS  Google Scholar 

  11. Sigel, M.M., L.L. Wellham, W. Licgter, L.E. Dudeck, J.L. Gargus, and A.H. Lucas: Anticellular and Antitumor Activity of Extracts from Typical Marine Invertebrates. In: Food-Drugs from the Sea Proceedings 1969 (H.W. Youngken, Jr., ed.), p. 281. Washington, D.C.: Marine Technology Society. 1969.

    Google Scholar 

  12. Whitson, D., and H.W. Titus: The Use of Starfish Meal in Chick Diets. Bull. Bingham Oceanog. Coll, 9, 24 (1945).

    Google Scholar 

  13. Lee, C.F.: US Fish Wildlife Service. Fish Leaflet, 391 (1951).

    Google Scholar 

  14. Heilbrunn, L.V., A.B. Chaet, A. Dunn, and W.L. Wilson: Antimitotic Substances from Ovaries. Biol. Bull., 106, 158 (1954).

    CAS  Google Scholar 

  15. Baltzer, F.: Über die Giftwirkung weiblicher Bonellia-Gewebe auf das Bonellia-Männchen und andere Organismen und ihre Beziehung zur Bestimmung des Geschlechts der Bonellienlarve. Mitt. Naturf. Ges. Bern, 8, 98 (1925).

    Google Scholar 

  16. Baltzer, F.: Über die Giftwirkung der weiblichen Bonellia und ihre Beziehung zur Geschlechtsbestimmung der Larve. Rev. Suisse Zool., 32, 87 (1925).

    Google Scholar 

  17. Friess, S.L., F.G. Standaert, E.R. Whitcomb, R.F. Nigrelli, J.D. Chanley, and H. Sobotka: Some Pharmacologie Properties of Holothurin A, a Glycosidic Mixture from the Sea Cucumber. Ann. NY Acad. Sci., 90, 893 (1960).

    CAS  Google Scholar 

  18. Schmeer, M.R., and C.V. Huala: Mercenene: In Vivo Effects of Mollusk Extracts on the Sarcoma 180. Ann. NY Acad. Sci., 118, 605 (1965).

    CAS  Google Scholar 

  19. Li, C.P., B. Prescott, and W.B. Jahnes: Antiviral Activity of a Fraction of Abalone Juice. Proc. Soc. Exp. Biol. Med, 109, 534 (1962).

    CAS  Google Scholar 

  20. Pettit, G.R., J.F. Day, J.L. Hartwell, and H.B. Wood: Antineoplastic Components of Marine Animals. Nature, 227, 962 (1970).

    CAS  Google Scholar 

  21. Pettit, G.R., J.L. Hartwell, and H.B. Wood: Arthropod Antineoplastic Agents. Cancer Res., 28, 2168(1968).

    CAS  Google Scholar 

  22. Pettit, G.R.: The Bryostatins. In: Progress in the Chemistry of Organic Natural Products, No. 57. Founded by Zechmeister, L. Herz, W., G.R. Kirby, W. Steglich, and C.H. Tamm, eds.), p. 153–195. Wien-New York: Springer-Verlag. 1991.

    Google Scholar 

  23. Pkttit, G.R.: Marine Animal and Terrestrial Plant Anticancer Constituents. Pure and Appl. Chem., 66, 2271 (1994).

    Google Scholar 

  24. Hyman, L.H.: The Invertebrates, Mollusca. American Museum of Natural History. New York: McGraw-Hill. 1967.

    Google Scholar 

  25. Eales, N.B.: L.M.B.C. Memoirs, Vol. 24. on “Typical British Marine Plants and Animals, Aplysia” (Hardman, W.A., and J. Johnstone, eds.), Liverpool University Press. 1921.

    Google Scholar 

  26. P liny: Historia Naturalis, Lib. 9, Lib. 32, ca. 60 A.D

    Google Scholar 

  27. Donati, G., and B. Porfirio: Marine Pharmacology and Toxicology. The Dolastatins. La Conchiglia 16, May, 1984.

    Google Scholar 

  28. Engel, H.: The genus Dolabella. Zool. Mededeel. Leyden, 24, 197 (1942).

    Google Scholar 

  29. See Ref. 1, Vol. 1, p. 709. 1965.

    Google Scholar 

  30. Pettit, G.R., R.H. Ode, C.L. Herald, R.B. Von Dreele, and C. Michel: The Isolation and Structure of Dolatriol. J. Amer. Chem. Soc., 98, 4677 (1976).

    CAS  Google Scholar 

  31. Bebbington, A.: Aplysiid Species from East Africa with Notes on the Indian Ocean Aplysiomorpha Gastropoda Opisthobranchia. Zool. J. Linn. Soc., 54, 63 (1974).

    Google Scholar 

  32. Kuwasawa, K., and K. Matsui: Postjunctional Potentials and Cardiac Acceleration in a Mollusc Dolabella auricularia. Experientia, 26, 1100 (1970).

    CAS  Google Scholar 

  33. Kuwasawa, S.: Heartbeat Inhibiting Effect of Inhibitory Connective Potential in Dolabella auricularia Heart. J. Physiol. Soc. Jap., 34, 453 (1972).

    Google Scholar 

  34. Kuwasawa, K.: Localization of Acetylcholine Response in the Heart of Dolabella auricularia. J. Physiol. Soc. Jpn., 35, 403 (1973).

    CAS  Google Scholar 

  35. Hill, R.B.: Effects of 5-Hydroxytryptamine on Action Potentials and on Contractile Force in the Ventricle of Dolabella auricularia. J. Exp. Biol., 61, 529 (1974).

    CAS  Google Scholar 

  36. Hill, R.B.: Effects of Acetylcholine on Resting and Action Potentials and on Contractile Force in the Ventricle of Dolabella auricularia. J. Exp. Biol., 61, 629 (1974).

    CAS  Google Scholar 

  37. Suzuki, S.: Localization of Intracellular Calcium and its Translocation During Mechanical Activity in the Smooth Muscle of a Mollusk Dolabella auricularia. J. Electron Microsc., 26, 253(1977).

    Google Scholar 

  38. Sugi, H., and S. Suzuki: Ultrastructural and Physiological Studies on the Longitudinal Body Wall Muscle of Dolabella auricularia. Part 1. Mechanical Response and Ultrastructure. J. Cell. Biol., 79, 454 (1978).

    CAS  Google Scholar 

  39. Marino, N.: Hemocyanin from Dolabella auricularia. Part 4. Dissociation by DEAE Cellulose. J. Biochem. (Tokyo), 72, 29 (1972).

    Google Scholar 

  40. Watson, M.: Ph.D. Thesis, University of Hawaii. Some Aspects of the Pharmacology, Chemistry and Biology of the Midgut Gland Toxins of Some Hawaiian Sea Hares, especially Dolabella auricularia and Aplysia plumonica. Ann Arbor, Michigan: University Microfilms, Inc. 1969.

    Google Scholar 

  41. Scheuer, P.J.: Recent Developments in the Chemistry of Marine Toxins Devries, A., and E. Kochva, eds.). Toxins of Animal and Plant Origin. Vol. 2. Proceedings of the 2nd International Symposium on Animal and Plant Toxins. Tel Aviv, Israel, Feb. 22–28, 1970. New York, London: Gordon and Breach Science Publishers.

    Google Scholar 

  42. Watson, M.: Midgut Gland Toxins of Hawaiian Sea Hares. Part 1. Isolation and Preliminary Toxicological Observations. Toxicon, 11, 259 (1973).

    CAS  Google Scholar 

  43. Pettit, G.R., C.L. Herald, R.H. Ode, P. Brown, D.J. Gust, and C. Michel: The Isolation of Loliolide from an Indian Ocean Opisthobranch Mollusc. J. Nat. Prod., 43, 752(1980).

    CAS  Google Scholar 

  44. Pettit, G.R., Y. Kamano, Y. Fuji, C.L. Herald, M. Inoue, P. Brown, D. Gust, K. Kitahara, J.M. Schidt, D.L. Doubek, and C. Michel: Marine Animal Biosynthetic Constituents for Cancer Chemotherapy. J. Nat. Proc., 44, 482 (1981).

    CAS  Google Scholar 

  45. Pettit, G.R., Y. Kamano, R. Aoyagi, C.L. Herald, D.L. Doubek, J.M. Schmidt, and J.J. Rudloe: Antineoplastic Agents 100. The Marine Bryozoan Amathia convoluta. Tetrahedron, 41, 985 (1985).

    CAS  Google Scholar 

  46. Pettit, G.R., Y. Kamano, P. Brown, D. Gust, M. Inoue, and C.L. Herald: Structure of the Cyclic Peptide Dolastatin 3 from Dolabella auricularia. J. Amer. Chem. Soc., 104, 905(1982).

    Google Scholar 

  47. Pettit, G.R., Y. Kamano, C.W. Holzapfel, W.J. Van Zyl, A.A. Tuinman, C.L. Herald, L. Baczynskyj, and J.M. Schmidt: The Structure and Synthesis of Dolastatin 3. J. Amer. Chem. Soc., 109, 7581 (1987).

    CAS  Google Scholar 

  48. Pettit, G.R., Y. Kamano, C.L. Herald, Y. Fuji, H. Kizu, M.R. Boyd, F.E. Boettner, D.L. Doubek, J.M. Schmidt, J.-C. Chapuis, and C. Michel: Isolation of Dolastatins 10-15 from the Marine Mollusc Dolabella auricularia. Tetrahedron, 49, 9151 (1993).

    CAS  Google Scholar 

  49. Pettit, G.R., Y. Kamano, C.L. Herald, A.A. Tuinman, F.E. Boettner, H. Kizu, J.M. Schmidt, L. Baczynskyj, K.B. Tomer, and R.J. Bontems: The Isolation and Structure of a Remarkable Marine Animal Antineoplastic Constituent: Dolastatin 10. J. Amer. Chem. Soc., 109, 6883(1987).

    Google Scholar 

  50. Pettit, G.R., Y. Kamano, H. Kizu, C. Dufresne, C.L. Herald, R. Bontems, J.M. Schmidt, F.E. Boettner, and R.A. Nieman: Isolation and Structure of the Cell Growth Inhibitory Depsipeptides Dolastatins 11 and 12. Heterocycles, 28, 553 (1989).

    CAS  Google Scholar 

  51. Pettit, G.R., Y. Kamano, C.L. Herald, C. Dufresne, R.L. Cerny, D.L. Herald, J.M. Schmidt, and H. Kizu: Isolation and Structure of the Cytostatic Depsipeptide Dolastatin 13 from the Sea Hare Dolabella auricularia. J. Amer. Chem. Soc., 111, 5015 (1989).

    CAS  Google Scholar 

  52. Pettit, G.R., Y. Kamano, C.L. Herald, C. Dufresne, R.E. Bates, and J.M. Schmidt: Antineoplastic Agents 190. Isolation and Structure of the Cyclodepsipeptide Dolastatin 14. J. Org. Chem., 55, 2989 (1990).

    CAS  Google Scholar 

  53. Pettit, G.R., Y. Kamano, C. Dufresne, R.C. Cerny, C.L. Herald, and J.M. Schmidt: Isolation and Structure of the Cytostatic Linear Depsipeptide Dolastatin 15. J. Org. Chem., 54, 6005(1989).

    CAS  Google Scholar 

  54. Sone, H., T. Nemoto, M. Ojika, and K. Yamada: Isolation, Structure, and Synthesis of Dolastatin C, a New Depsipeptide from the Sea Hare Dolabella auricularia. Tetrahedron Lett., 34, 8445 (1993).

    CAS  Google Scholar 

  55. Sone, H., T. Nemoto, H. Ishiwata, M. Ojika, and K. Yamada: Isolation, Structure, and Synthesis of Dolastatin D, a Cytotoxic Cyclic Depsipeptide from the Sea Hare Dolabella auricularia. Tetrahedron Lett., 34, 8449 (1993).

    CAS  Google Scholar 

  56. Yamada, K.: Private communication.

    Google Scholar 

  57. Sone, H., T. Nemoto, and K. Yamada: Doliculols A and B, the Non-halogenated C15 Acetogenins with Cyclic Ether from the Sea Hare Dolabella auricularia. Tetrahedron Lett., 34, 3461(1993).

    Google Scholar 

  58. Ishiwata, H., H. Sone, H. Kigoshi, and K. Yamada: Enantioselective Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide of Marine Origin, and Structure-Cytotoxicity Relationships of Synthetic Doliculide Congeners. Tetrahedron, 50, 12853 (1994).

    CAS  Google Scholar 

  59. Yamazaki, M: Antitumor and Antimicrobial Glycoproteins from Sea Hares. Comp. Biochem. Physiol, 105C, 141 (1993).

    CAS  Google Scholar 

  60. Pettit, G.R., D. Kantoci, D.L. Doubek, B.E. Tucker, W.E. Pettit, and R.M. Schroll: Isolation of the Nickel-Chlorin Chelate Tunichlorin from the South Pacific Sea Hare Dolabella auricularia. J. Nat. Prod., 56, 1981 (1993).

    CAS  Google Scholar 

  61. Pettit, G.R., P.S. Nelson, and C.W. Holzapfel: Synthesis of the cyclo-[(gly)Thz-(R)-and cyclo-[(gly)Thz-(S)-(gln)Thz-L-Val-L-Leu-L-Pro] Isomers of Dolastatin 3. J. Org. Chem., 50, 2654(1985).

    CAS  Google Scholar 

  62. Pettit, G.R., and C.W. Holzapfel: Synthesis of the Modified Dolastatin 3 Sequence cyclo-[L-Val-L-Leu-L-Pro-(R, S)-(gln)Thz-(gly)Thz]. J. Org. Chem, 51, 4586 (1986).

    CAS  Google Scholar 

  63. Pettit, G.R., and C. W. Holzapfel: Synthesis of the Dolastatin 3 Isomer cyclo-[L-Pro-L-Leu-L-Val-(R, S)-(gln)Thz-(gly)Thz]. J. Org. Chem., 51, 4580 (1986).

    CAS  Google Scholar 

  64. Holzapfel, C.W., and G.R. Pettit: Synthesis of the Dolastatin Thiazole Amino Acid Component (gln)Thz. J. Org. Chem, 50, 2323 (1985).

    CAS  Google Scholar 

  65. Eckart, K., U. Schmidt, and H. Shwarz: Amino Acids and Peptides; 60. Synthesis of Biologically Active Cyclopeptides; 10. Synthesis of 16 Structural Isomers of Dolastatin 3; II: Synthesis of the Linear Educts and the Cyclopeptides. Liebigs Ann. Chem, 1940 (1986).

    Google Scholar 

  66. Schmidt, U., and R. Utz: Synthetic Studies on the Elucidation of the Structure and Configuration of Dolastatin 3. Angew Chem, Int. Ed. Engl., 23, 725 (1984).

    Google Scholar 

  67. Hamada, Y., K. Kohda, and T. Shioiri: Proposed Structure of the Cyclic Peptide Dolastatin 3, A Powerful Cell Growth Inhibitor, Should Be Revised! Tetrahedron Lett., 25, 5303(1984).

    CAS  Google Scholar 

  68. Schmidt, U., and D. Weller: Total Synthesis of Ulithiacyclamide. Tetrahedron Lett., 27, 3495(1986).

    Google Scholar 

  69. Schmidt, U., R. Utz, A. Lieberknecht, H. Griesser, B. Potzolli, J. Bahr, K. Wagner, and P. Fischer: Sequenzierung von Thiazolaminosäuren enthaltenden Cyclopentapeptiden (“Dolastatin 3”) durch FAB/MSMS. Synthesis, 236 (1987).

    Google Scholar 

  70. Bernier, J.-L., R. Houssin, and J.-P. Henichart: Analog of Dolastatin 3. Synthesis, 1H-NMR Studies and Spatial Conformation. Tetrahedron, 42, 2695 (1986).

    CAS  Google Scholar 

  71. Holzapfel, C.W., G.R. Pettit, and G.M. Cragg: Biosynthetic Product Molecular Weight Determimations by Solution Phase Secondary Ion Mass Spectrometry Employing Group 1A Metal Salts. J. Nat. Prod., 48, 513 (1985).

    CAS  Google Scholar 

  72. Pettit, G.R., S.B. Singh, F. Hogan, P. Lloyd-Williams, D.L. Herald, D.D. Burkett, and PJ. Clewlow: The Absolute Configuration and Synthesis of Natural (−)-Dolastatin 10. J. Amer. Chem. Soc., 111, 5463 (1989).

    CAS  Google Scholar 

  73. Hayashi, K., Y. Hamada, and T. Shioiri: Synthetic Study on Dolastatin 10, an Antineoplastic Pentapeptide of Marine Origin. In: Peptide Chemistry (YANAIHARA, N., ed.), p. 291. Osaka: Protein Research Foundation. 1990.

    Google Scholar 

  74. Kano, S., Y. Yuasa, and S. Shibuya: Highly Diastereoselective Synthesis of N-Boc Dolaisoleuine, Unusual Amino Acid in Dolastatin 10. Heterocycles, 31, 1597 (1990).

    CAS  Google Scholar 

  75. Maugras, I., J. Poncet, and P. Jouin: Stereocontrolled Synthesis of N, O-Di-methyl-γ-Amino-β-Hydroxy Acids: Analogues of the (R)-Melle-Ψ(CHOMe)-Gly Residue of the Cytotoxic Marine Pseudopeptide Dolastatin 10. Tetrahedron, 46, 2807 (1990).

    CAS  Google Scholar 

  76. Bredenkamp, M.W., C.W. Holzapfel, R.M. Snyman, and W.J. Van Zyl: Observations on the Hantzsch Reaction: Synthesis of N-tBoc-S-Dolaphenine. Synth. Commun., 22, 3029(1992).

    CAS  Google Scholar 

  77. Hamada, Y., K. Hayashi, and T. Shioiri: Efficient Stereoselective Synthesis of Dolastatin 10, an Antineoplastic Peptide from a Sea Hare. Tetrahedron Lett., 32, 931 (1991).

    CAS  Google Scholar 

  78. Tomioka, K., M. Kanai, and K. Koga: An Expeditious Synthesis of Dolastatin 10. Tetrahedron Lett., 32, 2395 (1991).

    CAS  Google Scholar 

  79. Shioiri, T., K. Hayashi, and Y. Hamada: Stereoselective Synthesis of Dolastatin 10 and Its Congeners. Tetrahedron, 49, 1913 (1993).

    CAS  Google Scholar 

  80. Roux, F., I. Maugras, J. Poncet, G. Niel, and P. Jouin: Synthèse de la Dolastatine 10 et de la [R-Doe]-Dolastatine 10. Tetrahedron, 50, 5345 (1994).

    CAS  Google Scholar 

  81. Ireland, C.M., and P.J. Scheuer: Ulicyclamide and Ulithiacyclamide, Two New Small Peptides from a Marine Tunicate. J. Amer. Chem. Soc., 102, 5688 (1980).

    CAS  Google Scholar 

  82. Ireland, C.M., A.R. Durso, JR., R.A. Newman, and M.P. Hacker: Antineoplastic Cyclic Peptides from the Marine Tunicate Lissoclinum Patella. J. Org. Chem., 47, 1807 (1982).

    CAS  Google Scholar 

  83. Biskupiak, J.E., and C.M. Ireland: Absolute Configuration of Thiazole Amino Acids in Peptides. J. Org. Chem., 48, 2302 (1983).

    CAS  Google Scholar 

  84. Hamamoto, Y., M. Endo, M. Nakagawa, T. Nakanishi, and K. Mizukawa: A New Cyclic Peptide, Ascidiacyclamide, Isolated from Ascidian. J. Chem. Soc., Chem. Commun., 323 (1983).

    Google Scholar 

  85. Wasylyk, J.M., J.E. Biskupiak, C.E. Costello, and C.M. Ireland: Cyclic Peptide Structures from the Tunicate Lissoclinum Patella by FAB Mass Spectrometry. J. Org. Chem., 48, 4445 (1983).

    CAS  Google Scholar 

  86. Hamada, Y., S. Kato, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 51. A Synthesis of Ascidiacyclamide, a Cytotoxic Cyclic Peptide from Ascidian — Determination of Its Absolute Configuration. Tetrahedron Lett., 26, 3223 (1985).

    CAS  Google Scholar 

  87. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 58. A Synthesis of Patellamide A, a Cytotoxic Cyclic Peptide from a Tunicate. Revision of Its Proposed Structure. Tetrahedron Lett., 26, 6501 (1985).

    CAS  Google Scholar 

  88. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 55. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic Peptides from a Tunicate. 1. Their Proposed Structures Should Be Corrected. Tetrahedron Lett., 26, 5155(1985).

    Google Scholar 

  89. Hamada, Y., M. Shibata, and T. Shioiri: New Methods and Reagents in Organic Synthesis. 56. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic peptides from a Tunicate. 1. Their Real Structures have been Determined by Their Syntheses. Tetrahedron Lett., 26, 5159 (1985).

    CAS  Google Scholar 

  90. Schmidt, U., R. Utz, and P. Gleich: What is the Structure of the Patellamides? Tetrahedron Lett., 26, 4367 (1985).

    CAS  Google Scholar 

  91. Schmidt, U., and H. Griesser: Total Synthesis and Structure Determination of Patellamide B. Tetrahedron Lett., 27, 163 (1986).

    CAS  Google Scholar 

  92. Kato, S., Y. Hamada, and T. Shioiri: Total Synthesis of Ulithiacyclamide, a Strong Cytotoxic Cyclic Peptide. Tetrahedron Lett., 27, 2653 (1986).

    CAS  Google Scholar 

  93. Schmidt, U., and P. Gleich: Total Synthesis of Ulicyclamide. Angew. Chem., Int. Ed. Engl., 24, 569 (1985).

    Google Scholar 

  94. Bredenkamp, M., C. Holzapfel, and W. Van Zyl: The Chiral Synthesis of Thiazole Amino Acid Enantiomers. Synth. Commun., 20, 2235 (1990).

    CAS  Google Scholar 

  95. Kelly, R.C., I. Gebhard, and N. Wicnienski: Synthesis of (R)-and (S)-(glu)Thz and the Corresponding Bisthiazole Dipeptide of Dolastatin 3. J. Org. Chem., 51, 4590 (1986).

    CAS  Google Scholar 

  96. Pettit, G.R., F. Hogan, D.D. Burkett, S.B. Singh, D. Kantoci, J. Srirangam, and M.D. Williams: The Dolastatins 16. Synthesis of Dolaphenine. Heterocycles, 39, 81 (1994).

    CAS  Google Scholar 

  97. Parikh, J.R., and W. Von E. Doering: Sulfur Trioxide in the Oxidation of Alcohols by Dimethyl Sulfoxide. J. Amer. Chem. Soc., 89, 5505 (1967).

    CAS  Google Scholar 

  98. Fatiadi, A.J.: Active Manganese Dioxide Oxidation in Organic Chemistry. Synthesis, 65, 133 (1976).

    Google Scholar 

  99. Hayashi, K., Y. Hamada, and T. Shioiri: Stereoselective Total Synthesis of Dolastatin 10 Utilizing the Evans-Aldol Reaction. In: Third Symposium on the Chemistry of Natural Products. Osaka. 1991.

    Google Scholar 

  100. Irako, N., Y. Hamada, and T. Shioiri: A New Efficient Synthesis of (S)-Dolaphenine ((S)-2-Phenyl-l-(2-thiazolyl)ethylamine), the C-Terminal Unit of Dolastatin 10. Tetrahedron, 48, 7251 (1992).

    CAS  Google Scholar 

  101. Schmidt, U., P. Gleich, H. Griesser, and R. Utz: Synthesis of Optically Active 2-(l-Hydroxyalkyl)-thiazole-4-carboxylic Acids and 2-(l-Aminoalkyl)-thiazole-4-carboxylic Acids. Synthesis, 992 (1986).

    Google Scholar 

  102. Rinehart, K.L., R. Sakai, V. Kishore, D.W. Sullins, and K.-M. Li: Synthesis and Properties of the Eight Isostatine Stereoisomers. J. Org. Chem., 57, 3007 (1992).

    CAS  Google Scholar 

  103. Rinehart, K.L., B. Kishore, S. Nagarajan, R.J. Lake, J.B. Gloer, F.A. Bozich, K.-M. Li, R.E. Maleczka, JR., W.L. Todsen, M.H.G. Munro, D.W. Sullins, and R. Sakai: Total Synthesis of Didemnins A, B, and C. J. Amer. Chem. Soc., 109, 6846 (1987).

    CAS  Google Scholar 

  104. Schmidt, U., M. Kroner, and H. Griesser: Total Synthesis of the Didemnins-2. Synthesis of Didemnin A, B, C and Prolyldidemnin A. Tetrahedron Lett., 29, 4407 (1988).

    CAS  Google Scholar 

  105. Hamada, Y., Y. Kondo, M. Shibata, and T. Shioiri: Efficient Total Synthesis of Didemnins A and B. J. Amer. Chem. Soc., 111, 669 (1989).

    CAS  Google Scholar 

  106. Maibaum, J., and D.H. Rich: Inhibition of Porcine Pepsin by Two Substrate Analogues Containing Statine. The Effect of Histidine at the P2 Subsite on the Inhibition of Aspartic Proteinases. J. Med. Chem., 31, 625 (1988).

    CAS  Google Scholar 

  107. Wagner, I., and H. Musso: New Naturally Occurring Amino Acids. Angew. Chem., Int. Ed. Engl., 22, 816(1983).

    Google Scholar 

  108. Ewing, W.R., B.D. Harris, K.L. Bhat, and M.M. Jouillié: Synthetic Studies of the Detoxin Complex. 1. Total Synthesis of ( − )-Detoxinine. Tetrahedron, 42, 2421 ( 1986).

    Google Scholar 

  109. Hagiwara, H., K. Kimura, and H. Uda: High Diastereoselection in the Aldol Reaction of the Bistrimethylsilyl Enol Ether of Methyl Acetoacetate with 2-Benzyloxyhexanal. Synthesis of (−)-Pestalotin. J. Chem. Soc., Perkin Trans. 1, 693 (1992).

    Google Scholar 

  110. Franck-Nhumann, M., P.-J. Colson, P. Geoffroy, K.M. Taba: The Aldol Condensation Reaction of Diene (Tricarbonyl)iron Complexes. From Metal Coordinated Trimethylsilyl Enol Ethers to Polyols of Known Configuration. Tetrahedron Lett., 33, 1903 (1992).

    Google Scholar 

  111. Kobayashi, S., and I. Hachiya: The Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media. Tetrahedron Lett., 33, 1625 (1992).

    CAS  Google Scholar 

  112. Devant, R.M., and H.-E. Radunz: A Short Novel and Efficient Asymmetric Synthesis of Statine Analogues. Tetrahedron Lett., 29, 2307 (1988).

    CAS  Google Scholar 

  113. Wuts, P.G.M., and S.R. Putt: Synthesis of N-Boc-Statine and epi-Statine. Synthesis, 951 (1989).

    Google Scholar 

  114. Pettit, G.R., S.B. Singh, D.L. Herald, P. Lloyd-Williams, D. Kantoci, D.D. Burkett, J. Barkóczy, F. Hogan, and T.R. Wardlaw: The Dolastatins. 17. Synthesis of Dolaproine and Related Diastereoisomers. J. Org. Chem., 59, 6287 (1994).

    CAS  Google Scholar 

  115. Smith, A.B., III, T.L. Leenay, H.-J. Liu, L.A.K. Nelson, and R.G. Ball: A Caveat on the Swern Oxidation. Tetrahedron Lett., 29, 49 (1988).

    CAS  Google Scholar 

  116. Braun, M., and R. Devant: Effective Synthetic Equivalents of a Chiral Acetate Enolate. Tetrahedron Lett., 25, 5031 (1984).

    CAS  Google Scholar 

  117. Kantoci, D., G.R. Pettit, and T.R. Wardlaw: Efficient Separation of Dolaproine Stereoisomers by Optimization of a Three Component Chromatographic Solvent System. J. Liq. Chromatogr., 13, 3915 (1990).

    CAS  Google Scholar 

  118. Pettit, G.R., S.B. Singh, F. Hogan, and D.D. Burkett: Chiral Modifications of Dolastatin 10: The Potent Cytostatic Peptide(19aR)-Isodolastatin 10. J. Med. Chem., 33, 2177(1990).

    Google Scholar 

  119. Diem, M.J., D.F. Burow, and J.L. Fry: Oxonium Salt Alkylation of Structurally and Optically Labile Alcohols. J. Org. Chem., 42, 180 (1990).

    Google Scholar 

  120. Walker, M.A., and C.H. Heathcock: Extending the Scope of the Evans Asymmetric Aldol Reaction: Preparation of Anti and Non-Evans Syn Aldols. J. Org. Chem., 56, 5747(1991).

    Google Scholar 

  121. Gage, J.R., and D.A. Evans: Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S*, 3S*)-3-Hydroxy-3-Phenyl-2-Methylpropanoic Acid. Org. Synth., 68, 83(1989).

    Google Scholar 

  122. Van Draanen, N.A., S. Arseniyadis, M.T. Crimmins, and C.H. Heathcock: Protocols for the Preparation of Each of the Four Possible Stereoisomeric α-Alkyl-β-hydroxy Carboxylic Acids from a Single Chiral Aldol Reagent. J. Org. Chem., 56, 2499 (1991).

    Google Scholar 

  123. Heathcock, C.H.: Understanding and Controlling Diastereofacial Selectivity in Carbon-Carbon Bond-Forming Reactions. Aldrichimica Acta, 23, 99 (1990).

    CAS  Google Scholar 

  124. Danda, H., M.M. Hansen, and C.H. Heathcock: Reversal of Stereochemistry in the Aldol Reactions of a Chiral Boron Enolate. J. Org. Chem., 55, 173 (1990).

    CAS  Google Scholar 

  125. Pettit, G.R., S.B. Singh, J.K. Srirangam, F. Hogan-Pierson, and M.D. Williams: The Dolastatins. 19. Synthesis of Dolaisoleuine. J. Org. Chem., 59, 1796 (1994).

    CAS  Google Scholar 

  126. Pettit, G.R., M.D. Williams, J.K. Srirangam, F. Hogan, N.L. Benoiton, and D. Kantoci: The dolastatins 25. Conformational isomerism of N-benzyloxycarbonyl-N-methylisoleucinol and related substances. J. Chem. Soc., Perkin Trans. 2, 919 (1995).

    Google Scholar 

  127. Mcdermott, J.R., and N.L. Benoiton: N-Methylamino Acids in Peptides Synthesis. III. Racemization During Deprotection by Saponification and Acidolysis. Can. J. Chem., 51, 2555 (1973).

    CAS  Google Scholar 

  128. Mcdermott, J.R., and N.L. Benoiton: N-Methylamino Acids in Peptides Synthesis. IV. Racemization and Yields in Peptide-Bond Formation. Can. J. Chem., 51, 2562 (1973).

    CAS  Google Scholar 

  129. Mcdermott, J.R., and N.L. Benoiton: N-Methylamino Acids in Peptides Synthesis. II. A New Synthesis of N-Benzyloxycarbonyl N-Methylamino Acids. Can. J. Chem., 51, 1915(1973).

    CAS  Google Scholar 

  130. Evans, D.A., J. Bartroli, and T.L. Shih: Enantioselective Aldol Condensations. 2. Erythro-Selective Chiral Aldol Condensations via Boron Enolates. J. Amer. Chem. Soc., 103, 2127(1981).

    CAS  Google Scholar 

  131. Boger, D.L., and T.T. Curran: Synthesis of the Lower Subunit of Rhizoxin. J. Org. Chem., 50, 1830(1985).

    Google Scholar 

  132. Gutierrez, C.G., and L.R. Summerhays: Organotin-Mediated Selective Desulfurization: Tri-N-butyltin Hydride Reduction of Unsymmetric Sulfides. J. Org. Chem., 49, 5206(1984).

    CAS  Google Scholar 

  133. Anderson, G.W., and F.M. Callahan: t-Butyl Esters of Amino Acids and Peptides and Their Use in Peptide Synthesis. J. Amer. Chem. Soc., 82, 3359 (1960).

    Google Scholar 

  134. Cook, B., R.R. Hill, and G.E. Jeffs: Efficient One-Step Synthesis of Diastereoisomeric Cyclic Dipeptides from Amino Acids: Three Diastereoisomers of Cyclo-L-isoleucyl-L-isoleucine. J. Chem. Soc., Perkin Trans. 1, 1199 (1992).

    Google Scholar 

  135. Abraham, R.J., J.T. Jackson, and W.A. Thomas: The Fixed Conformation of the Leucyl Side-Chain in a Tripeptide. Org. Mag. Res., 14, 543 (1980).

    CAS  Google Scholar 

  136. Torii, K., and Y. Iitaka: The Crystal Structure of L-Isoleucine. Acta Crystallogr., B27, 2237(1971).

    Google Scholar 

  137. Coggins, J.J.R., and N.L. Benoiton: Synthesis of N-Methylamino Acid Derivative from Amino Acid Derivatives Using Sodium Hydride-Methyl Iodide. Can. J. Chem., 49, 1968(1971).

    Google Scholar 

  138. Steinauer, R., F.M.F. Chen, and N.L. Benoiton: N-Methylamino Acids in Peptide Synthesis. Int. J. Peptide Protein Res., 26, 109 (1985).

    CAS  Google Scholar 

  139. Pettit, G.R., J. Barkoczy, J.K. Srirangam, S.B. Singh, D.L. Herald, M.D. Williams, D. Kantoci, F. Hogan, and T.L. Groy: The Dolastatins. 22. Synthesis of Boc-dolaproinyl-dolaphenine and Four Related Chiral Isomers. J. Org. Chem., 59, 2935(1994).

    Google Scholar 

  140. Wenger, R.M.: Synthesis of Cyclosporine and Analogues: Structural Requirements for Immunosuppressive Activity. Angew. Chem., Int. Ed. Engl., 24, 77 (1985).

    Google Scholar 

  141. Coste, J., M.-M. Dufour, A. Pantaloni, and B. Castro: BROP: A New Reagent for Coupling N-Methylated Amino Acids. Tetrahedron Lett., 31, 669 (1990).

    CAS  Google Scholar 

  142. Yamada, S., I. Ikota, T. Shioiri, and S. Tachibana: Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC), Two New Reagents for Solid-Phase Peptide Synthesis and Their Application to the Synthesis of Porcine Motulin. J. Amer. Chem. Soc., 97, 7174 (1975).

    CAS  Google Scholar 

  143. Bowman, R.E., and H.H. Stroud: N-Substituted Amino-acids. Part 1. A New Method of Preparation of Dimethylamino-acids. J. Chem. Soc., 1342 (1950).

    Google Scholar 

  144. Pettit, G.R., J.K. Srirangam, S.B. Singh, M.D. Williams, D.L. Herald, J. Barkoczy, D. Kantoci, and F. Hogan: The Dolastatins. 24. Synthesis of (−)-dolastatin 10. J. Chem. Soc., Perkin Trans. 1, 859 (1996).

    Google Scholar 

  145. Shioiri, T.: Total Synthesis of Dolastatin 10, an Antitumor Marine Peptide Containing Unusual Amino Acids. Chem. Soc. Jpn., 52, 392 (1994).

    CAS  Google Scholar 

  146. Pettit, G.R., J.K. Srirangam, J. Barkoczy, M.D. Williams, K.P.M. Durkin, M.R. Boyd, R. Bai, E. Hamel, J.M. Schmidt, and J.-C. Chapuis: Antineoplastic Agents 337. Synthesis of dolastatin 10 structural modifications. Anti-Cancer Drug Design, 10, 529 (1995).

    CAS  Google Scholar 

  147. Aguilar, E., and A.I. Meyers: Reinvestigation of a Modified Hantzsch Thiazole Synthesis. Tetrahedron Lett., 35, 2473 (1994).

    CAS  Google Scholar 

  148. Pettit, G.R., D. Kantoci, D.L. Herald, J. Barkoczy, and J.A. Slack: Procedures for the Analyses of Dolastatins 10 and 15 by High Performance Liquid Chromatography. J. Liq. Chromatogr., 17, 191 (1994).

    CAS  Google Scholar 

  149. Pettit, G.R., J.K. Srirangam, D.L. Herald, and E. Hamel: The Dolastatins. 21. Synthesis, X-ray Crystal Structure, and Molecular Modeling of (6R)-Isodolastatin 10. J. Org. Chem., 59, 6127 (1994).

    CAS  Google Scholar 

  150. Hamel, E.: Interactions of Tubulin with Small Ligands. In: Microtubule Proteins (Avila, J., ed.), p. 89. Boca Raton: CRC Press. 1990.

    Google Scholar 

  151. Bai, R., G.R. Pettit, and E. Hamel: Structure-Activity Studies with Chiral Isomers and with Segments of the Antimitotic Marine Peptide Dolastatin 10. Biochem. Pharmacol., 40, 1859(1990).

    CAS  Google Scholar 

  152. Bai, R., G.R. Pettit, and E. Hamel: Binding of Dolastatin 10 to Tubulin at a Distinct Site for Peptide Antimitotic Agents Near the Exchangeable Nucleotide and Vinca Alkaloid Sites. J. Biol. Chem., 265, 17141 (1990).

    CAS  Google Scholar 

  153. Bai, R., G.R. Pettit, and E. Hamel: Dolastatin 10, A Powerful Cytostatic Peptide Derived from a Marine Animal: Inhibition of Tubulin Polymerization Mediated through the Vinca Alkaloid Binding Domain. Biochem. Pharmacol., 39, 1941 (1990).

    CAS  Google Scholar 

  154. Bai, R., M.C. Roach, S.K. Jayaram, J. Barkoczy, G.R. Pettit, R.F. Luduena, and E. Hamel: Differential Effects of Active Isomers, Segments, and Analogs of Dolastatin 10 on Ligand Interactions with Tubulin. Biochem. Pharmacol., 45, 1503 (1993).

    CAS  Google Scholar 

  155. Kirst, H.A., E.F. Szymanski, D.E. Dormann, J.L. Occolowitz, N.D. Jones, M.O. Chaney, R.L. Hamill, and M.M. Hoehn: Structure of Althiomycin. J. Antibiotics, 28, 286(1975).

    CAS  Google Scholar 

  156. Cardellina, J.H. II, F.-J. Marner, and R.E. Moore: Malyngamide A, a Novel Chlorinated Metabolite of the Marine Cyanophyte Lyngbya majuscula. J. Amer. Chem. Soc., 101, 240 (1979).

    CAS  Google Scholar 

  157. Cardellina, J.H. II, and R.E. Moore: The Structure of Pukeleimides A, B, C, D, E, F, and G. Tetrahedron Lett., 2007 (1979).

    Google Scholar 

  158. Von Hofheinz, W., and W.E. Oberhansli: Dysidin, ein neuartiger, chlorhaltiger Naturstoff aus dem Schwamm Dysidea herbacea. Helv. Chim. Acta, 60, 660 (1977).

    CAS  Google Scholar 

  159. Gebreyesus, T., T. Yosief, S. Carmely, and Y. Kashman: Dysidamide, a Novel Hexachloro-metabolite from a Red Sea Sponge Dysidea sp. Tetrahedron Lett., 29, 3863 (1988).

    CAS  Google Scholar 

  160. Oikawa, Y., K. Sugano, and O. Yonemitsu: Meldrum’s Acid in Organic Synthesis. 2. A General and Versatile Synthesis of β-Keto Esters. J. Org. Chem., 43, 2087 (1978).

    CAS  Google Scholar 

  161. Pettit, G.R., T.J. Thornton, J.T. Mullaney, M.R. Boyd, D.L. Herald, S.B. Singh, and E.J. Flahive: The Dolastatins 20. A Convenient Route to Dolastatin 15. Tetrahedron, 50, 12097(1994).

    Google Scholar 

  162. Jouin, P., B. Castro, and D. Nisato: Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid. J. Chem. Soc., Perkin Trans. 1, 1177 ( 1987).

    Google Scholar 

  163. Patino, N., Frerot, N. Galeotti, J. Poncet, J. Coste, M.-N. Dufour, and P. Jouin: Total Synthesis of the Proposed Structure of Dolastatin 15. Tetrahedron, 48, 4115 (1992).

    CAS  Google Scholar 

  164. Ishiwata, H., H. Sone, H. Kigoshi, and K. Yamada: Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide from the Japanese Sea hare Dolabella auricularia. J. Org. Chem., 59, 4712 (1994).

    CAS  Google Scholar 

  165. Ojika, M., H. Kigoshi, T. Ishigaki, and K. Yamada: Further Studies on Aplyronine A, an Antitumor Substance Isolated from the Sea Hare Aplysia kurodai. Tetrahedron Lett., 34, 8501(1993).

    Google Scholar 

  166. Kigoshi, H., M. Ojika, T. Ishigaki, K. Suenaga, T. Mutou, A. Sakakura, T. Ogawa, and K. Yamada: Total Synthesis of Aplyronine A, a Potent Antitumor Substance of Marine Origin. J. Amer. Chem. Soc., 116, 7443 (1994).

    CAS  Google Scholar 

  167. Ojika, M., T. Yoshida, and K. Yamada: Aplysepine, a Novel 1, 4-Benzodiazepine Alkaloid from the Sea Hare Aplysia kurodai. Tetrahedron Lett., 33, 5307 (1993).

    Google Scholar 

  168. Quentmeier, H., S. Brauer, G.R. Pettit, and H.D. Drexler: Cytostatic Effects of Dolastatin 10 and Dolastatin 15 on Human Leukemia Cell Lines. Leukemia and Lymphoma, 6, 245(1992).

    Google Scholar 

  169. Steube, K.G., H. Quentmeier, G.R. Pettit, T. Pietsch, S. Brauer, D. Grunicke, S.M. Gignac, and H.G. Drexler: Inhibition of Cellular Proliferation by the Natural Peptides Dolastatin 10 and Dolastatin 15. Mol. Biol. Haematapoiesis, 2, 567 (1992).

    Google Scholar 

  170. Steube, K.G., D. Grunicke, T. Pietsch, S.M. Gignac, G.R. Pettit, and H.G. Drexler: Dolastatin 10 and Dolastatin 15: Effects of Two Natural Peptides on Growth and Differentiation of Leukemia Cells. Leukemia, 6, 1048 (1992).

    CAS  Google Scholar 

  171. Hu, Z.-B., S.M. Gignac, H. Quentmeier, G.R. Pettit, and H.G. Drexler: Effects of Dolastatins on Human B-Lymphocytic Leukemia Cell Lines. Leukemia Res., 17, 333 (1993).

    CAS  Google Scholar 

  172. Kim, I.K., B.S. Lee, Y.T. Hong, H.S. Choi, and N.Y. Kwon: Synthesis of Dolastatin 10 Analogues. J. Korean Chem. Soc., 38, 763 (1994).

    CAS  Google Scholar 

  173. Luduena, R.F., M.C. Roach, V. Prasad, and G.R. Pettit: Interaction of Dolastatin 10 with Bovine Brain Tubulin. Biochem. Pharmacol., 43, 539 (1992).

    CAS  Google Scholar 

  174. Bai, R., G.F. Taylor, J.M. Schmidt, M.D. Williams, J.A. Kepler, G.R. Pettit, and E. Hamel: Interaction of Dolastatin 10 with Tubulin: Induction of Aggregation and Binding and Dissociation Reactions. Mol. Pharmacol. 47, 965 (1995).

    CAS  Google Scholar 

  175. Bai, R., S.J. Friedman, G.R. Pettit, and E. Hamel: Dolastatin 15, a Potent Antimitotic Depsipeptide Derived from Dolabella auricularia. Interaction with Tubulin and Effects on Cellular Microtubules. Biochem. Pharmacol., 43, 2637 (1992).

    CAS  Google Scholar 

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  1. Cancer Research Institute and Department of Chemistry, Arizona State University, Tempe, Arizona, USA

    G. R. Pettit

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Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz

  2. Chemistry Department, The University of Glasgow, Glasgow, Scotland

    G. W. Kirby

  3. Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, USA

    R. E. Moore

  4. Institut für Organische Chemie der Universität München, München, Federal Republic of Germany

    W. Steglich

  5. Institut für Organische Chemie der Universität Basel, Basel, Switzerland

    Ch. Tamm

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Pettit, G.R. (1997). The Dolastatins. In: Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 70. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6551-5_1

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