Synthetic Applications (Total Synthesis and Natural Product Synthesis)

  • Hirofumi Tohma
  • Yasuyuki Kita
Chapter
First Online:
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 224)

Abstract

Recently, hypervalent iodine reagents have been used extensively in organic synthesis. In particular, (diacyloxyiodo)benzenes such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA) have received a great deal of attention due to low toxicity, ready availability, easy handling, and reactivities similar to that of heavy metal reagents and anodic oxidation. A variety of available reactions for natural product syntheses have been developed using PIDA, PIFA, and other iodine(III or V) reagents. These reactions are expected to be utilized for pharmaceutical and agrochemical process due to their safety, mild reaction conditions and high yields. This review focuses on recent progress in the use of hypervalent iodine reagents toward total syntheses of various biologically active natural products involving quinones, alkaloids, flavonoids, sugars, and other antibiotics.

Keywords

Hypervalent iodine reagents Total synthesis Natural products 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Banks DF (1966) Chem Rev 66:243CrossRefGoogle Scholar
  2. 2.
    Varvoglis A (1981) Chem Soc Rev 10:377CrossRefGoogle Scholar
  3. 3.
    Umemoto T (1983) J Synth Org Chem Jpn 41:251Google Scholar
  4. 4.
    Koser GF (1983) In: Patai S, Rappoport Z (eds) The Chemistry of Functional Groups Supplement D, chapter 18 and 25. Wiley, New YorkGoogle Scholar
  5. 5.
    Varvoglis A (1984) Synthesis 709Google Scholar
  6. 6.
    Moriarty RM, Prakash O (1986) Acc Chem Res 19:244CrossRefGoogle Scholar
  7. 7.
    Ochiai M, Nagao Y (1986) J Synth Org Chem Jpn 44:660Google Scholar
  8. 8.
    Merkushev EB (1987) Russ Chem Rev (Engl Transl) 56:826CrossRefGoogle Scholar
  9. 9.
    Ochiai M (1989) Rev Heteroatom Chem 2:92Google Scholar
  10. 10.
    Moriarty RM, Vaid RK (1990) Synthesis 431Google Scholar
  11. 11.
    Moriarty RM, Vaid RK, Koser GF (1990) Synlett 365Google Scholar
  12. 12.
    Varvoglis A (1992) The organic chemistry of polycoordinated iodine. VCH, New YorkGoogle Scholar
  13. 13.
    Kita Y, Tohma H, Yakura T (1992) Trends in Organic Chemistry 3:113Google Scholar
  14. 14.
    Prakash O, Rani N, Tanwar MP, Moriarty RM (1995) Contemp Org Synth 2:121CrossRefGoogle Scholar
  15. 15.
    Kitamura T (1995) J Synth Org Chem Jpn 53:893Google Scholar
  16. 16.
    Stang PJ, Zhdankin VV (1996) Chem Rev 96:1123CrossRefGoogle Scholar
  17. 17.
    Kita Y, Takada T, Tohma H (1996) Pure Appl Chem 68:627CrossRefGoogle Scholar
  18. 18.
    Varvoglis A (1997) Hypervalent iodine in organic synthesis. Academic, San DiegoGoogle Scholar
  19. 19.
    Kitamura T, Fujiwara Y (1997) Org Prep Proced Int 29:409CrossRefGoogle Scholar
  20. 20.
    Moriarty RM, Prakash O (1998) Adv Heterocyclic Chem 69:1Google Scholar
  21. 21.
    Wirth T, Hirt UH (1999) Synthesis:1271Google Scholar
  22. 22.
    Ochiai M, Kitagawa Y (2000) J Synth Org Chem Jpn 58:1048Google Scholar
  23. 23.
    Vaino AR, Szarek WA (2001) Adv Carbohydrate Chem & Biochem 56:9CrossRefGoogle Scholar
  24. 24.
    Togo H, Katohgi M (2001) Synlett 565Google Scholar
  25. 25.
    Koser GF (2001) Aldrichimica Acta 34:89Google Scholar
  26. 26.
    Wirth T (2001) Angew Chem 113:2889; Angew Chem Int Ed 40:2812CrossRefGoogle Scholar
  27. 27.
    Tamura Y, Yakura T, Haruta J, Kita Y (1987) J Org Chem 52:3927CrossRefGoogle Scholar
  28. 28.
    Lewis N, Wallbank P (1987) Synthesis 1103Google Scholar
  29. 29.
    Pelter A, Elgendy S (1988) Tetrahedron Lett 29:677CrossRefGoogle Scholar
  30. 30.
    Tamura Y, Yakura T, Tohma H, Kikuchi K, Kita Y (1989) Synthesis 126Google Scholar
  31. 31.
    Barret R, Daudon M (1991) Tetrahedron Lett 32:2133CrossRefGoogle Scholar
  32. 32.
    Hwang JT, Liao CC (1991) Tetrahedron Lett 32:6583CrossRefGoogle Scholar
  33. 33.
    Mitchell AS, Russell RA (1993) Tetrahedron Lett 34:545CrossRefGoogle Scholar
  34. 34.
    Gao SY, Ko S, Lin YL, Peddinti K, Liao CC (2001) Tetrahedron 57:297CrossRefGoogle Scholar
  35. 35.
    Wang S, Gates BD, Swenton JS (1991) J Org Chem 56:1979CrossRefGoogle Scholar
  36. 36.
    Gates BD, Dalidowicz P, Tebben A, Wang S, Swenton JS (1992) J Org Chem 57:2135CrossRefGoogle Scholar
  37. 37.
    Pelter A, Ward RS (2001) Tetrahedron 57:273CrossRefGoogle Scholar
  38. 38.
    Quideau S, Pouységu L, Oxoby M, Looney MA (2001) Tetrahedron 57:319CrossRefGoogle Scholar
  39. 39.
    Callinan A, Gary YC, Morrow GW, Swenton JS (1990) Tetrahedron Lett 31:4551CrossRefGoogle Scholar
  40. 40.
    Swenton JS, Callinan A, Chen Y, Rohde JJ, Kerns ML, Morrow GW (1996) J Org Chem 61:1267CrossRefGoogle Scholar
  41. 41.
    Kita Y, Tohma H, Kikuchi K, Inagaki M, Yakura T (1991) J Org Chem 56:435CrossRefGoogle Scholar
  42. 42.
    Kaçan M, Kouyuncu D, McKillop A (1993) J Chem Soc Perkin Trans 1 1771CrossRefGoogle Scholar
  43. 43.
    Murakata M, Yamada K, Hoshino O (1994) J Chem Soc Chem Commun 443Google Scholar
  44. 44.
    Kita Y, Yakura T, Tohma H, Kikuchi K, Tamura Y (1989) Tetrahedron Lett 30:1119CrossRefGoogle Scholar
  45. 45.
    Kita Y, Takada T, Ibaraki M, Gyoten M, Mihara S, Fujita S, Tohma H (1996) J Org Chem 61:223CrossRefGoogle Scholar
  46. 46.
    Szántay C, Blaskó G, Bárczai-Beke M (1980) Tetrahedron Lett 21:3509CrossRefGoogle Scholar
  47. 47.
    White JD, Chong WKM, Thirring K (1983) J Org Chem 48:2300CrossRefGoogle Scholar
  48. 48.
    White JD, Caravatti G, Kline TB, Edstrom E, Rice KC, Brossi A (1983) Tetrahedron 39:2393CrossRefGoogle Scholar
  49. 49.
    Beringer FM, Falk RA, Rarniol M, Lillien I, Masullo G, Mausner M, Sommer E (1959) J Am Chem Soc 81:342CrossRefGoogle Scholar
  50. 50.
    Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T (1991) Tetrahedron Lett 32:4321CrossRefGoogle Scholar
  51. 51.
    Kita Y, Tohma H, Hatanaka K, Takada T, Fujita S, Mitoh S, Sakurai H, Oka S (1994) J Am Chem Soc 116:3684CrossRefGoogle Scholar
  52. 52.
    Kita Y, Takada T, Mihara S, Whelan BA, Tohma H (1995) J Org Chem 60:7144CrossRefGoogle Scholar
  53. 53.
    Arisawa M, Ramesh NG, Nakajima M, Tohma H, Kita Y (2001) J Org Chem 66:59CrossRefGoogle Scholar
  54. 54.
    Kita Y, Gyoten M, Ohtsubo M, Tohma H, Takada T (1996) Chem Commun 1481Google Scholar
  55. 55.
    Takada T, Arisawa M, Gyoten M, Hamada R, Tohma H, Kita Y (1998) J Org Chem 63: 7698CrossRefGoogle Scholar
  56. 56.
    Tohma H, Morioka H, Takizawa S, Arisawa M, Kita Y (2001) Tetrahedron 57:345CrossRefGoogle Scholar
  57. 57.
    Hamamoto H, Anilkumar G, Tohma H, Kita Y (2002) Chem Commun 450Google Scholar
  58. 58.
    Kita Y, Egi M, Okajima A, Ohtsubo M, Takada T, Tohma H (1996) Chem Commun 1491Google Scholar
  59. 59.
    Kita Y, Egi M, Ohtsubo M, Saiki T, Takada T, Tohma H (1996) Chem Commun 2225Google Scholar
  60. 60.
    Moreno I, Tellitu I, Etayo J, SanMartín R, Domínguez E (2001) Tetrahedron 57:54CrossRefGoogle Scholar
  61. 61.
    Moreno I, Tellitu I, San Martín R, Domínguez E (2001) Synlett 1161Google Scholar
  62. 62.
    Nicolaou KC, Sugita K, Baran PS, Zhong YL (2001) Angew Chem 113:213; Angew Chem Int Ed 40:207CrossRefGoogle Scholar
  63. 63.
    Nicolaou KC, Zhong YL, Baran PS, Sugita K (2001) Angew Chem 113:2203; Angew Chem Int Ed 40:2145CrossRefGoogle Scholar
  64. 64.
    Nicolaou KC, Baran PS, Zhong YL, Vega JA (2000) Angew Chem 112:2625; Angew Chem Int Ed 39:2525CrossRefGoogle Scholar
  65. 65.
    Ochiai M, Kunishima M, Nagao Y, Fuji K, Shiro M, Fujita E (1986) J Am Chem Soc 108:8281CrossRefGoogle Scholar
  66. 66.
    Feldman KS, Bruendl MM, Schildknegt K, Bohnstedt AC (1996) J Org Chem 61:5440CrossRefGoogle Scholar
  67. 67.
    Feldman KS, Mareska DA (1999) J Org Chem 64:5650CrossRefGoogle Scholar
  68. 68.
    Moriarty RM, Prakash O, Vaid RK, Zhao L (1989) J Am Chem Soc 111:6443CrossRefGoogle Scholar
  69. 69.
    Moriarty RM, Prakash O (1985) J Org Chem 50:151CrossRefGoogle Scholar
  70. 70.
    Magnus P, Lacour J (1992) J Am Chem Soc 114:767CrossRefGoogle Scholar
  71. 71.
    Magnus P, Lacour J (1992) J Am Chem Soc 114:3993CrossRefGoogle Scholar
  72. 72.
    Magnus P, Lacour J, Weber W (1993) J Am Chem Soc 115:9347CrossRefGoogle Scholar
  73. 73.
    Magnus P, Lacour J, Evans PA, Roe MB, Hulme C (1996) J Am Chem Soc 118:3406CrossRefGoogle Scholar
  74. 74.
    Nicolaou KC, Zhong YL, Baran PS (2000) J Am Chem Soc 122:7596CrossRefGoogle Scholar
  75. 75.
    Nicolaou KC, Montagnon T, Baran PS, Zhong YL (2002) J Am Chem Soc 124:2245CrossRefGoogle Scholar
  76. 76.
    Hashem MA, Jung A, Ries M, Kirschning A (1998) Synlett 195Google Scholar
  77. 77.
    Tamura Y, Yakura T, Haruta J, Kita Y (1985) Tetrahedron Lett 26:3837CrossRefGoogle Scholar
  78. 78.
    Kita Y, Yakura T, Terashi H, Haruta J, Tamura Y (1989) Chem Pharm Bull 37:891Google Scholar
  79. 79.
    Radhakrishna AS, Parham ME, Riggs RM, Louden GM (1979) J Org Chem 44:1746CrossRefGoogle Scholar
  80. 80.
    Louden MG, Radhakrishna AS, Almond MR, Blodgett JK, Boutin RH (1984) J Org Chem 49: 4272CrossRefGoogle Scholar
  81. 81.
    Moriarty RM, Chany CJ II, Vaid RK, Prakash O, Tuladhar SM (1993) J Org Chem 58:2478CrossRefGoogle Scholar
  82. 82.
    Stork G, Zhao K (1989) Tetrahedron Lett 30:287CrossRefGoogle Scholar
  83. 83.
    Kikugawa Y, Kawase M (1990) Chem Lett 581Google Scholar
  84. 84.
    Kirihara M, Yokoyama S, Kakuda H, Momose T (1995) Tetrahedron Lett 36:6907Google Scholar
  85. 85.
    Kishi Y, Nakatsuka S, Fukuyama T, Havel M (1973) J Am Chem Soc 95:6493CrossRefGoogle Scholar
  86. 86.
    Corey EJ, Wu LI (1993) J Am Chem Soc 115:9327CrossRefGoogle Scholar
  87. 87.
    Génisson Y, Tyler PC, Young RN (1994) J Am Chem Soc 116:759CrossRefGoogle Scholar
  88. 88.
    Shair MD, Yoon TY, Mosny KK, Chou TC, Danishefsky SJ (1996) J Am Chem Soc 118:9509CrossRefGoogle Scholar
  89. 89.
    Myers AG, Tom NJ, Fraley ME, Cohen SB, Madar DJ (1997) J Am Chem Soc 119:6072CrossRefGoogle Scholar
  90. 90.
    Taylor RJK, Alcaraz L, Kapfer-Eyer I, Macdonald G, Wei X, Lewis N (1998) Synthesis 775Google Scholar
  91. 91.
    Wipf P, Coish PDG (1999) J Org Chem 64:5053CrossRefGoogle Scholar
  92. 92.
    Carlini R, Higgs K, Older C, Randhawa S, Rodrigo R (1997) J Org Chem 62:2330CrossRefGoogle Scholar
  93. 93.
    Churcher I, Hallett D, Magnus P (1998) J Am Chem Soc 120:3518CrossRefGoogle Scholar
  94. 94.
    Kürti L, Szilágyi L, Antus S, Nógrádi M (1999) Eur J Org Chem 2579Google Scholar
  95. 95.
    Bergeron D, Brassard P (1992) Hetrocycles 34:1835Google Scholar
  96. 96.
    Kato N, Sugaya T, Mimura T, Ikuta M, Kato S, Kuge Y, Tomioka S, Kasai M (1997) Synthesis 625Google Scholar
  97. 97.
    Kinugawa M, Masuda Y, Arai H, Nishikawa H, Ogasa T, Tomioka S, Kasai M (1996) Synthesis 633Google Scholar
  98. 98.
    Rama Rao AV, Gurjar MK, Sharma PA (1991) Tetrahedron Lett 32:6613CrossRefGoogle Scholar
  99. 99.
    Wipf P, Kim Y, Fritch PC (1993) J Org Chem 58:7195CrossRefGoogle Scholar
  100. 100.
    McKillop A, McLaren L, Taylor RJK, Watson RJ, Lewis NJ (1996) J Chem Soc Perkin Trans 1:1385CrossRefGoogle Scholar
  101. 101.
    Gurjar MK, Bhaket P (2000) Heterocycles 53:143Google Scholar
  102. 102.
    Wipf P, Kim Y, Goldstein DM (1999) J Am Chem Soc 117:11106CrossRefGoogle Scholar
  103. 103.
    Pettus LH, Van De Water RW, Pettus TRR (2001) Org Lett 3:905CrossRefGoogle Scholar
  104. 104.
    Murakata M, Yamada K, Hoshino O (1998) Heterocycles 47:921CrossRefGoogle Scholar
  105. 105.
    Katoh T, Ohmori O, Iwasaki K, Inoue M (2002) Tetrahedron 58:1289CrossRefGoogle Scholar
  106. 106.
    Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T (1992) J Am Chem Soc 114:2175CrossRefGoogle Scholar
  107. 107.
    Tohma H, Harayama Y, Hashizume M, Iwata M, Egi M, Kita Y (2002) Angew Chem 114:358; Angew Chem Int Ed 41:348CrossRefGoogle Scholar
  108. 108.
    Pelter A, Satchwell P, Ward RS, Blake K (1995) J Chem Soc Perkin Trans 1 2201CrossRefGoogle Scholar
  109. 109.
    Ward RS, Pelter A, Abd-El-Ghani A (1996) Tetrahedron 52:1303CrossRefGoogle Scholar
  110. 110.
    Pelter A, Ward RS, Abd-El-Ghani A (1996) J Chem Soc Perkin Trans 1 1353CrossRefGoogle Scholar
  111. 111.
    Pelter A, Ward RS, Abd-El-Ghani A (1994) Tetrahedron Asymmetry 5:329CrossRefGoogle Scholar
  112. 112.
    Kita Y, Takada T, Gyoten M, Tohma H, Zenk MH, Eichhorn J (1996) J Org Chem 61:5857CrossRefGoogle Scholar
  113. 113.
    Kita Y, Arisawa M, Gyoten M, Nakajima M, Hamada R, Tohma H, Takada T (1998) J Org Chem 63:6625CrossRefGoogle Scholar
  114. 114.
    Pelish HE, Westwood NJ, Feng Y, Kirchhausen T, Shair MD (2001) J Am Chem Soc 123:6740CrossRefGoogle Scholar
  115. 115.
    Node M, Kodama S, Hamashima Y, Baba T, Hamamichi N, Nishide K (2001) Angew Chem 113:3150; Angew Chem Int Ed 40:3060CrossRefGoogle Scholar
  116. 116.
    Ley SV, Schucht O, Thomas AW, Murray PJ (1999) J Chem Soc Perkin Trans 1 1251CrossRefGoogle Scholar
  117. 117.
    Wipf P, Jung JK (1998) J Org Chem 63:3530CrossRefGoogle Scholar
  118. 118.
    Wipf P, Jung JK, Rodriguez S, Lazo JS (2001) Tetrahedron 57:283CrossRefGoogle Scholar
  119. 119.
    Scheffler G, Seike H, Sorensen EJ (2000) Angew Chem 112:4783; Angew Chem Int Ed 39: 4593CrossRefGoogle Scholar
  120. 120.
    Ousmer M, Braun NA, Bavoux C, Perrin M, Ciufolini MA (2001) J Am Chem Soc 123:7534CrossRefGoogle Scholar
  121. 121.
    Mizutani H, Takayama J, Soeda Y, Honda T (2002) Tetrahedron Lett 43:2411CrossRefGoogle Scholar
  122. 122.
    Kita Y, Watanabe H, Egi M, Saiki T, Fukuoka Y, Tohma H (1998) J Chem Soc Perkin Trans 1 635CrossRefGoogle Scholar
  123. 123.
    Tohma H, Egi M, Ohtsubo M, Watanabe H, Takizawa S, Kita Y (1998) Chem Commun 173Google Scholar
  124. 124.
    Kita Y, Egi M, Tohma H (1999) Chem Commun 143Google Scholar
  125. 125.
    Kita Y, Egi M, Takada T, Tohma H (1999) Synthesis 885Google Scholar
  126. 126.
    Arisawa M, Utsumi S, Nakajima M, Ramesh NG, Tohma H, Kita Y (1999) Chem Commun 469Google Scholar
  127. 127.
    Faul MM, Sullivan KA (2001) Tetrahedron Lett 42:3271CrossRefGoogle Scholar
  128. 128.
    Bringmann G, Tasler S (2001) Tetrahedron 57:331CrossRefGoogle Scholar
  129. 129.
    Nicolaou KC, Sugita K, Baran PS, Zhong YL (2002) J Am Chem Soc 124:2221CrossRefGoogle Scholar
  130. 130.
    Nicolaou KC, Baran PS, Zhong YL, Barluenga S, Hunt KW, Kranich R, Vega JA (2002) J Am Chem Soc 124:2233CrossRefGoogle Scholar
  131. 131.
    Hickey DMB, Leeson PD, Novelli R, Shah VP, Burpitt BE, Crawford LP, Davies BJ, Mitchell MB, Pancholi KD, Tuddenham D, Lewis NJ, O’Farrel C (1988) J Chem Soc Perkin Trans 1 3103CrossRefGoogle Scholar
  132. 132.
    de Sousa JDF, Rodrigues JAR, Abramovitch RA (1994) J Am Chem Soc 116:9745CrossRefGoogle Scholar
  133. 133.
    Kume M, Kubota T, Iso Y (1995) Tetrahedron Lett 36:8043CrossRefGoogle Scholar
  134. 134.
    Feldman KS, Masters KM, Di Florio R, Perkins AL, Cutarelli TD (2001) FIU (Forum on Iodine Utilization) report:the 4th Symposium on Iodine Utilization:5Google Scholar
  135. 135.
    Miki Y, Kobayashi S, Ogawa N, Hachiken H (1994) Synlett 1001Google Scholar
  136. 136.
    Litkei G, Gulácsi K, Antus S, Blaskó G (1995) Liebigs Ann 1711Google Scholar
  137. 137.
    Tamura Y, Sasho M, Ohe H, Akai S, Kita Y (1990) Tetrahedron Lett 26:1549CrossRefGoogle Scholar
  138. 138.
    Magnus P, Sebhat IK (1998) J Am Chem Soc 120:5341CrossRefGoogle Scholar
  139. 139.
    Wipf P, Kim HY (1993) J Org Chem 58:5592CrossRefGoogle Scholar
  140. 140.
    Romero AG, Darlington WH, McMillan MW (1997) J Org Chem 62:6582CrossRefGoogle Scholar
  141. 141.
    Kirihara M, Nishio T, Yokoyama S, Kakuda H, Momose T (1999) Tetrahedron 55:2911CrossRefGoogle Scholar
  142. 142.
    Lee E, Choi SJ, Kim H, Han HO, Kim YK, Min SJ, Son H, Lim SM, Jang WS (2002) Angew Chem 114:184; Angew Chem Int Ed 41:176CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2003

Authors and Affiliations

  • Hirofumi Tohma
    • 1
  • Yasuyuki Kita
    • 1
  1. 1.Graduate School of Pharmaceutical SciencesOsaka UniversitySuita, OsakaJapan

Personalised recommendations