Installation of carbon nucleophiles onto monoacetate of 4-cyclopentene-1,3-diol and synthesis of cyclopentanoids

Current Organic Chemistry

Volumn 7, Issue 2, 2003, Pages 133-147

  Kobayashi, Yuichi ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON;

ARYLATIONS; CARBON NUCLEOPHILES; CYCLOPENTENES; DIFFERENT SUBSTRATES; METHYL ESTERS; PRODUCT SELECTIVITIES;

REACTION INTERMEDIATES;

12 OXOPHYTODIENOIC ACID; 15 HYDROXY 9 OXOPROSTA 7,10,13 TRIENOIC ACID METHYL ESTER; 4 CYCLOPENTENE 1,3 DIOL ACETATIC ACID; ARISTEROMYCIN; BREFELDIN A; BREFELDIN C; CARBON; CARBOVIR; CLAVULONE DERIVATIVE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANOIC ACID; CYCLOPENTANOID DERIVATIVE; EGREGIACHLORIDE E; JASMONIC ACID; METHYLENOMYCIN A; MULTIFIDENE; PENTENOMYCIN; PROSTAGLANDIN A2; PROSTAGLANDIN E2; STRYCHNINE; UNCLASSIFIED DRUG;

ALKYLATION; ARYLATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; HYDROLYSIS; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037251786     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033373120     Document Type: Review

References (122)

1. (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533-1594.
2. (b) Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272.
3. (c) Noyori, R.; Suzuki, M. Angew. Chem. Int. Ed. Engl. 1984, 23, 847-876.
4. (d) Noyori, R.; Suzuki, M. Science 1993, 259, 44-45.
5. (e) Harre, M.; Raddatz, P.; Walenta, R.; Winterfeldt, E. Angew. Chem. Int. Ed. Engl. 1982, 21, 480-492.
6. (f) Kobayashi, Y. Trends Org. Chem. 1998, 7, 27-43.
7. (a) Deardorff, D. R.; Amador, R. B.; Morton, J. W.; Kim, H. Y.; Taniguchi, C. M.; Balbuena, A. A.; Warren, S. A.; Fanous, V.; Choe, S. W. T. Tetrahedron: Asymmetry 1999, 10, 2139-2152.
8. (b) Deardorff, D. R.; Windham, C. Q.; Craney, C. L. Org. Synth. 1998, Col. Vol. 9, 487-493.
9. (c) Johnson, C. R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287-7290.
10. (d) Sugai, T.; Moki, K. Synthesis 1988, 19-22.
11. (e) Deardorff, D. R.; Matthews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 27, 1255-1256.
12. (f) Laumen, K., Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1298-1299.
13. (g) Ghorpade, S. R.; Kharul, R. K.; Joshi, R. R.; Kalkote, U. R.; Ravindranathan, T. Tetrahedron: Asymmetry 1999, 10, 891-899.
14. (h) Johnson, C. R.; Baun, M. P. J. Am. Chem. Soc. 1993, 115, 11014-11015.
15. (i) Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582.
16. (j) Theil, F.; Ballschuh, S.; Schick, H.; Haupt, M.; Häfner, B.; Schwarz, S. Synthesis 1988, 540-541.
17. (k) Theil, F.; Schick, H.; Lapitskaya, M. A.; Pivnitsky, K. K. Liebigs Ann. Chem. 1991, 195-200.
18. (l) Laumen, K.; Reimerdes, E. H.; Schneider, M. Tetrahedron Lett. 1985, 26, 407-410.
19. (m) Laumen, K.; Schneider, M. Tetrahedron Lett. 1984, 25, 5875-5878
20. (n) Wang, Y.-F.; Chen, C. -S.; Girdaukas, G.; Sih, C. J. J. Am Chem. Soc. 1984, 106, 3695-3696.
21. (a) Deardorff, D. R.; Linde, R. G., II.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762
22. (b) Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776-5788.
23. (c) Deardorff, D. R.; Savin, K. A.; Justman, C. J.;KaranjawaLa, Z. E., Sheppeck J.E. II.; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61: 3616-3622.
24. (a) Crandall, J. K. Banks, D. B., Colyer, R. A.; Wilkins, R J.; Arrington, J. P. J Org Chem. 1968, 33, 423-425.
25. (b) Korach, M.; Nielsen, D. R.; Rideout, W. H. Org. Synth. 1973 Col. Vol. 5, 414-418. Preparation of 7 in detail is described in ref. if.
26. Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615-5618.
27. Deardorff, D. R.; Myles, D. C. Org. Synth. 1993, Co. Vol. 8, 13-16.
28. Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669-672.
29. Mikame, D.; Hamada, T.; Irie, R.; Katsuki, T. Synlett 1995, 827-828.
30. Kaneko, C.; Sugimoto, A.; Tanaka, S. Synthesis 1974, 876-877.
31. Curran, T. T.; Hay, D. A.; Koegel, C. P.; Evans, J. C. Tetrahedron 1997, 53, 1983-2004.
32. Duhamel, L.; Herman, T. Tetrahedron Lett. 1985, 26, 3099-3102.
33. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
34. Hess, H. M.; Brown, H. C. J. Org. Chem. 1967, 32, 4138-4139.
35. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-886.
36. (a) Asami, M. Tetrahedron Lett. 1985, 26, 5803-5806.
37. (b) Asami, M. Bull. Chem. Soc. Jpn. 1990, 63, 1402-1408.
38. (c) Asami, M.; Inoue, S. Tetrahedron 1995, 51, 11725-11730.
39. Bhuniya, D.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1996, 61, 6108-6113.
40. (a) Ito, M.; Murugesh, M. G.; Kobayashi, Y. Tetrahedron Lett. 2001, 42, 423-427.
41. (b) Ito, M.; Matsuumi, M.; Murugesh, M. G.; Kobayashi, Y. J. Org. Chem. 2001, 66, 5881-5889.
42. Related works: (c) ref. 21.
43. (d) Kobayashi, Y.; Ito, M.; Igarashi, J. Tetrahedron Lett. 2002, 43, 4829-4832.
44. (a) Goering, H. L.; Singleton, V. D. Jr. J. Am. Chem. Soc. 1976, 98, 7854-7855.
45. (b) Kreft, A. Tetrahedron Lett. 1977, 1035-1036.
46. (c) Tanigawa, Y.; Ohta, H.; Sonoda, A.; Murahashi, S.-I. J. Am. Chem. Soc. 1978, 100, 4610-4612.
47. (d) Gendreau, Y.; Normant, J. F. Tetrahedron 1979, 35, 1517-1521.
48. (e) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 2318-2325.
49. (f) Trost, B. M.; Klun, T. P. J. Org. Chem. 1980, 45, 4256-4257.
50. (g) Gallina, C. Tetrahedron Lett. 1982, 23, 3093-3096.
51. (h) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422-426.
52. (i) Goering, H. L.; Kantner, S. S.; Seitz, E. P., Jr. J. Org. Chem. 1985, 50, 5495-5499.
53. (j) Curran, D. P.; Chen, M.-H.; Leszczweski, D.; Elliott, R. L.; Rakiewicz, D. M. J. Org. Chem. 1986, 51, 1612-1614.
54. (k) Bäckvall, J.-E.; Sellén, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615-6621.
55. (l) Underiner, T. L.; Goering, H. L. J. Org. Chem. 1990, 55, 2757-2761.
56. (m) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207-1214.
57. (n) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94.
58. (a) Nakamura, E.; Mori, S. Angew. Chem. Int. Ed. Engl. 2000, 39, 3750-3771.
59. (b) Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
60. (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
61. (d) Yamamoto, Y. Angew. Chem. Int. Ed. Engl. 1986, 25, 947-1038.
62. (e) Liptshutz, B. H. In Organometallics in Synthesis; Schlosser, M. Ed.; Wiley: New York, 1994; chapter 4.
63. (f) Liptshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038.
64. (a) Bertz, S. H.; Chopra, A.; Eriksson, M.; Ogle, C. A.; Seagle, P. Chem. Eur. J. 1999, 2680-2691.
65. (b) Krause, N. Angew. Chem. Int. Ed. Engl. 1999, 38, 79-81.
66. Matsuumi, M.; Ito, M.; Kobauashi, Y. Synlett 2002, 1508-1510.
67. Marino, J. P.; Fernández De La Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4898-4913.
68. Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. Synlett 1997, 477-478.
69. Badalassi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, A.; Feringa, B.L. Tetrahedron Lett. 1998, 39, 7795-7798.
70. (a) Partridge, J. J.; Chadha, N. K.; Uskokovi'c, M. R. J. Am. Chem. Soc. 1973, 95, 532-540.
71. (b) Grethe, G.; Sereno, J.; Williams, T.H.; Uskokovi'c, M. R. J. Org. Chem. 1983, 48, 5315-5317.
72. (c) Partridge, J. J.; Chadha, N. K.; Uskokovi'c, M. R. J. Am. Chem. Soc. 1973, 95, 7171-7172.
73. (d) Chadha, N. K.; Batcho, A. D.; Tang, P. C.; Courtney, L. F.; Cook, C. M.; Wovkulich, P. M.; Uskokovi'c, M. R. J. Org. Chem. 1991, 56, 4714-4718.
74. (a) Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 160-161.
75. (b) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723-727.
76. (a) Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833-4840.
77. (b) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C. Synth. Commun. 1997, 27, 1267-1271.
78. (a) Kobayashi, Y.; Mozojiri, R.; Ikeda, E. J. Org. Chem. 1996, 61, 5391-5399.
79. (b) Kobayashi, Y. Recent Res. Devel. Org. Chem. 1999, 3, 61-77.
80. (c) Kobayashi, Y. Synth. Org. Chem. Jpn. 1999, 57, 845-855.
81. (a) Kobayashi, Y.; Takahisa, E.; Usmani, S. B. Tetrahedron Lett. 1998, 39, 597-600.
82. (b) Usmani, S. B.; Takahisa, E.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 601-604.
83. (c) Tokoro, Y.; Kobayashi, Y. Chem. Commun. 1999, 807-808.
84. (d) Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 6125-6128.
85. (a) Echavarren, A. M.; Tueting, D. R.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 4039-4041.
86. (b) Tueting, D. R.; Echavarren, A. M.; Stille, J. K. Tetrahedron 1989, 45, 979-992.
87. (a) Marino, J. P.; Fernández De La Pradilla, R.; Laborde, E. J. Org. Chem. 1984; 49, 5279-5280.
88. (b) Marino, J. P.; Kelly, M. G. J. Org. Chem. 1981, 46, 4389-4393.
89. Marino, J. P.; Farina, J. S. J. Org. Chem. 1976, 41, 3213-3215.
90. Tucci, F. C.; Chieffi, A.; Comasseto, J. V.; Marino, J. P. J. Org. Chem. 1996, 61, 4975-4989.
91. (a) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969-5972.
92. (b) Deardorff, D. R.; Shulman, M. J.; Sheppeck, J. E., II. Tetrahedron Lett. 1989, 30, 6625-6628.
93. (c) Mazón, A.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron Lett. 1997, 38, 2167-2170.
94. Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809-4812.
95. (a) Baertschi, S. W.; Ingram, C. D.; Harris, T. M.; Brash, A. R. Biochemistry 1988, 27, 18-24.
96. (b) Crombie, L.; Morgan, D. O. J. Chem. Soc., Perkin Trans. 1 1991, 581-587.
97. (c) Laudert, D.; Henning, P.; Stelmach, B. A.; Müller, A.; Andert, L.; Weiler, E. W. Analytical Biochem. 1997, 247, 211-217.
98. (d) Hamberg, M.; Hughes, M. A. Lipids 1988, 23, 469-475.
99. (e) Hamberg, M.; Miersch, O.; Sembdner, G. Lipids 1988, 23, 521-524.
100. Vick, B. A.; Zimmerman, D. C. Biochem. Biophys. Res. Commun. 1983, 111, 470-477.
101. (a) Creelman, R. A.; Mullet, J. E. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1997, 48, 355-381.
102. (b) Sembdner, G.; Parthier, B. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 569-589.
103. (c) Hamberg, M.; Gardner, H. W. Biochim. Biophys. Acta 1992, 1165, 1-18.
104. Kobayashi, Y.; Matsuumi, M. Tetrahedron Lett. 2002, 43, 4361-4364.
105. (a) Grieco, P. A.; Abood, N. J. Org. Chem. 1989, 54, 6008-6010.
106. (b) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin Trans. 1 1991, 1981-1991.
107. (a) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999-7006.
108. (b) Takahashi, K.; Sato, H.; Mikami, K.; Nakai, T. Chem. Lett. 1989, 247-250.
109. Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. J. Chem. Soc., Perkin I 1981, 1407-1410.
110. (a) Chapleo, C. B.; Finch, M. A. W.; Lee, T. V.; Roberts, S. M.; Newton, R. F. J. Chem. Soc., Perkin I 1980, 2084-2087.
111. (b) Newton, R. F.; Reynolds, D. P.; Davies, J.; Kay, P. B.; Roberts, S. M.; Wallace, T. W. J. Chem. Soc., Perkin Trans. I 1983, 683-685.
112. (a) Sugiura, S.; Toru, T.; Tanaka, T.; Hazato, A.; Okamura, N.; Bannai, K.; Manabe, K.; Kurozumi, S.; Noyori, R. Chem. Pharm. Bull. 1984, 32, 4658-4661.
113. (b) Suzuki, M.; Morita, Y.; Koyano, H.; Koga, M.; Noyori, R. Tetrahedron 1990, 46, 4809-4822.
114. (a) Kato, T.; Fukushima, M.; Kurozumi, S.; Noyori, R. Cancer Res. 1986, 46, 3538-3542.
115. (b) Suzuki, M.; Kiho, T.; Tomokiyo, K.; Furuta, K.; Fukushima, S.; Takeuchi, Y.; Nakanishi, M.; Noyori, R. J. Med. Chem. 1998, 41, 3084-3090.
116. Suzuki, M.; Mori, M.; Niwa, T.; Hirata, R.; Furuta, K.; Ishikawa, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 2376-2385.
117. Noyori, R.; Koyano, H.; Mori, M.; Hirata, R.; Shiga, Y.; Kokura, T.; Suzuki, M. Pure Appl. Chem. 1994, 66, 1999-2005.
118. Kobayashi, Y.; Murugesh, M. G.; Nakano, M. Tetrahedron Lett. 2001, 42, 1703-1707.
119. (a) Posner, G. H.; Gurria, G. M.; Babiak, K. A. J. Org. Chem. 1977, 42, 3173-3180.
120. (b) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666-3672.
121. (c) Another example: William, A. D.; Kobayashi, Y. Org. Lett. 2001, 3, 2017-2020.
122. Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234-236.