Enantioselective total synthesis of (+)-brefeldin A and 7-epi-brefeldin A

Journal of Organic Chemistry

Volumn 69, Issue 11, 2004, Pages 3857-3865

  Wu, Yikang ^a   Shen, Xin ^a   Yang, Yong Qing ^a   Hu, Qi ^a   Huang, Jia Hui ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; REACTION KINETICS; REDUCTION; SOLUBILITY; SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

CYCLOPENTENONES; ENANTIOSELECTIVITY; INTERMOLECULAR ADOLIZATION;

NITROGEN COMPOUNDS;

7 EPIBREFELDIN A; BREFELDIN A; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG ISOLATION; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 2442645214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049971d     Document Type: Article

References (117)

1. Singleton, V. L.; Bohonos, N.; Ullstrup, A. J. Nature (London) 1958, 181, 1072.
2. (a) Betina, V.; Nemec, P.; Dobias, J.; Barath, A. Folia Microbiol. (Prague) 1962, 7, 353.
3. (b) Harri, E.; Loeffler, W.; Sigg, H. P.; Stahelin, H.; Tamm, C. Helv. Chim. Acta 1963, 46, 1235.
4. (c) Betina, V.; Fuska, J.; Kjaer, A.; Kutkova, M.; Nemec, P.; Shapiro, R. H. J. Antibiot., Ser. A. 1966, 19, 115.
5. (d) Suzuki, Y.; Tanaka, H.; Aoki, H.; Tamura, T. Agric. Biol. Chem. 1970, 34, 395.
6. (e) Mirrington, R. N.; Ritchie, E.; Shoppe, C. W.; Sternhell, S.; Taylor, W. C. Aust. J. Chem. 1966, 19, 1265.
7. (f) Coombe, R. G.; Jacobs, J. J.; Watson, T. R. Aust. J. Chem. 1968, 21, 783.
8. (g) Mortimer, P. H.; DiMenaa, M. E.; White, E. P. Mycotoxic Fugi, Mycotoxins, Mycotoxicoses 1978, 2, 219; Chem. Abstr. 1978, 89, 1453z.
9. (g) Mortimer, P. H.; DiMenaa, M. E.; White, E. P. Mycotoxic Fugi, Mycotoxins, Mycotoxicoses 1978, 2, 219; Chem. Abstr. 1978, 89, 1453z.
10. (h) Entwistle, I. D.; Howard, C. C.; Johnstone, R. A. W. Phytochemsitry 1974, 13, 173.
11. (i) Jinnouchi, H.; Yagishita, K. Jpn. J. Antibiot. 1981, 34, 51; Chem. Abstr. 1981, 95, 74439.
12. (i) Jinnouchi, H.; Yagishita, K. Jpn. J. Antibiot. 1981, 34, 51; Chem. Abstr. 1981, 95, 74439.
13. (j) Evans, G.; Cartwright, J. B.; White, N. H. Plant Soil 1967, 26, 253; Chem. Abstr. 1967, 66, 102574v.
14. Evans, G.; Cartwright, J. B.; White, N. H. Plant Soil 1967, 26, 253; Chem. Abstr. 1967, 66, 102574v.
15. Weber, H. P.; Hauser, D.; Sigg, H. P. Helv. Chim. Acta 1971, 54, 2763.
16. (a) Betina, V.; Drobnica, L.; Nemec, P.; Zemanova, M. J. Antibiot., Ser. A 1964, 17, 93.
17. (b) Betina, V.; Betinova, M.; Kutkova, M. Arch. Mikrobiol. 1966, 55, 1.
18. (c) Hayashi, T.; Takatsuki, A.; Tamura, G. J. Antibiot. 1974, 27, 65.
19. (a) Tamura, G.; Ando, K.; Suzuki, S.; Takatsuki, A.; Arina, K. J. Antibiot. 1968, 21, 160.
20. (b) Takatsuki, A.; Yamaguchi, I.; Tamura, G.; Misato, T.; Amrima, K. J. Antibiot. 1969, 22, 442.
21. (a) Betina, V. Neoplasma 1969, 16, 23.
22. (b) Horakova, K.; Betina, V. Neoplasma 1974, 24, 21 and references therein.
23. Bacikova, D.; Betina, V.; Nemec, P. Naturwissenschaften 1965, 51, 445.
24. Konno, S.; Mordente, J. A.; Chen, Y.; Wu, J. M.; Tazaki, H.; Mallouh, C. Mol. Urol. 1998, 2, 7; Chem. Abstr. 1998, 128: 317011.
25. Konno, S.; Mordente, J. A.; Chen, Y.; Wu, J. M.; Tazaki, H.; Mallouh, C. Mol. Urol. 1998, 2, 7; Chem. Abstr. 1998, 128: 317011.
26. Satoh, M.; Ito, A.; Nojiri, H.; Handa, K.; Numahata, K.; Ohyama, C.; Saito, S.; Hoshi, S.; Hakomori, S. Int. J. Oncol. 2001, 19, 723; Chem. Abstr. 2002, 136, 276937
27. Satoh, M.; Ito, A.; Nojiri, H.; Handa, K.; Numahata, K.; Ohyama, C.; Saito, S.; Hoshi, S.; Hakomori, S. Int. J. Oncol. 2001, 19, 723; Chem. Abstr. 2002, 136, 276937
28. Storck, J.; Vahland, M.; Breer, T.; Zimmermann, E. R. Br. J. Haematol. 1997, 99, 555; Chem. Abstr. 1998, 128, 100229
29. Storck, J.; Vahland, M.; Breer, T.; Zimmermann, E. R. Br. J. Haematol. 1997, 99, 555; Chem. Abstr. 1998, 128, 100229
30. Cuconati, A.; Molla, A.; Wimmer, E. J. Virol. 1998, 72, 6456; Chem. Abstr. 1998, 129, 183886
31. Cuconati, A.; Molla, A.; Wimmer, E. J. Virol. 1998, 72, 6456; Chem. Abstr. 1998, 129, 183886
32. Shao, R. G.; Shimiau, T.; Pommier, Y. Exp. Cell Res. 1998, 227, 190.
33. Corey, E. J.; Wollenberg, R. H. Tetrahedron Lett. 1976, 4705.
34. For syntheses of BFA before 1997, see reviews, e.g.: Kobayashi, Y.; Watatani, K. Yuki Gosei Kagaku Kyokaishi 1997, 55, 110; Chem. Abstr. 1997, 126, 185901.
35. For syntheses of BFA before 1997, see reviews, e.g.: Kobayashi, Y.; Watatani, K. Yuki Gosei Kagaku Kyokaishi 1997, 55, 110; Chem. Abstr. 1997, 126, 185901.
36. For recent total syntheses (from 1997 on) of BFA, see: (a) Haynes, R. K. ; Lam, W. W.-L.; Yeung, L. L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552.
37. (b) Wang, Y.; Romo, D. Org. Lett. 2002, 4, 3231.
38. (c) Trost, B. M.; Crawley, M. L. J. Am. Chem. Soc. 2002, 124, 9328.
39. (d) Suh, Y. G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Kim, S.-H.; Park, H.-J. J. Org. Chem. 2002, 67, 4127.
40. (e) Kim, D.; Lee, J.; Shim, P. J.; Lim, J. I.; Doi, T.; Kim, S. J. Org. Chem. 2002, 67, 772.
41. (f) Kim, D.; Lee, J.; Shim, P. J.; Lim, J. I.; Jo, H.; Kim, S. J. Org. Chem. 2002, 67, 764.
42. (g) For a brief communication of the present work, see: Wu, Y.-K.; Shen, X.; Yang, Y.-Q.; Hu, Q.; Huang, J.-H. Tetrahedron Lett. 2004, 45, 199.
43. (a) Argade, A. B.; Haugwitz, R. D.; Devraj, R.; Kozlowski, J.; Fanwick, P. E.; Cushman, M. J. Org. Chem. 1998, 63, 273.
44. (b) Argade, A. B.; Devraj, R.; Vroman, J. A.; Haugwitz, R. D.; Hollingshead, M.; Cushman, M. J. Med. Chem. 1998, 41, 3337.
45. (a) Zhu, J.-W.; Nagasawa, H.; Nagura, F.; Mohamad, S. B.; Uto, Y.; Ohkura, K.; Hori, H. Biorg. Med. Chem. 2000, 8, 455.
46. (b) Zhu, J.-W.; Hori, H.; Nojiri, H.; Tsukuda, T.; Taira, Z. Bioorg. Med. Chem. Lett. 1997, 7, 139.
47. (c) Weigele, M.; Loewe, M. F.; Poss, C. S.; Lazarova, T. (Ariad Pharmaceuticals, Inc., USA). PCT Int. Appl. WO 9521614 Al, Aug 17, 1995, 54 pp; Chem. Abstr. 1996, 124, 8507.
48. (d) Weigele, M.; Loewe, M. F.; Poss, C. S. (Ariad Pharmaceuticals, Inc., USA). U.S. US 5516921 A, May 14, 1996, 14 pp; Chem. Abstr. 1996, 125, 58201.
49. (a) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
50. (b) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000,2, 775.
51. (c) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
52. (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
53. (b) Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 1939.
54. Gorst-Allman, C. P.; Stevn, P. S. J. Chem. Soc., Perkin Trans. 1 1982, 2387.
55. Gais, H.-J.; Lied, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 145.
56. (a) Achab, S.; Das, B. C. J. Chem. Soc., Perkin Trans. 1 1990, 2863.
57. (b) Mzzina, E.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1989, 854.
58. (c) Tadano, K.-I.; Miyazaki, M.; Ogawa, S.; Suami, T. J. Org. Chem. 1988, 53, 1574.
59. (d) Tadano, K.-I.; Ueno, Y.; Fukabori, C.; Hotta, Y.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1727.
60. Wu, Y.-K.; Shen, X. Tetrahedron: Asymmetry 2000, 11, 4359.
61. (a) Landor, S. R.; Landor, P. D.; Kalli, M. J. Chem. Soc., Perkin Trans. 1 1983, 2921.
62. (b) Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
63. (a) Schuricht, U.; Endler, K.; Hennig, L.; Findeisen, M.; Welzel, P. J. Prakt. Chem. 2000, 342, 761.
64. (b) Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. J. Org. Chem. 1995, 60, 564.
65. Cox, C. M.; Whitting, D. A. J. Chem. Soc., Perkin Trans. 1 1991, 1907-1911.
66. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067.
67. Wu, Y.-K.; Shen, X.; Tang, C.-J.; Chen, Z.-L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802.
68. Karimi, B.; Seradj, H.; Ebrahimian, G.-R. Synlett 1999, 1456.
69. Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 20, 307.
70. (a) We attempted to convert the acyl-thiazolidinethione 7b into the corresponding methyl ester or aldehyde as reported (ref 18b) by Crimmins. Testing the two conversions (using MeOH/imidazole or DIBAL-H to cleave the thiazolidinethione auxiliary) on 7b resulted in neither 33 (at low temperatures no reactions occurred, while at higher temperatures a complicated product mixture was obtained) nor 34 (extremely slow, with prolonged reaction/more forcing conditions leading to substantial amounts of diol 11), suggesting that the facile cleavage of the thiazolidinethione observed by Crimmins might be applicable only to those nonhindered acyl-thiazolidinethiones.
71. (b) We tried (Scheme 8) to convert diol 11 into di-TBS ether 35 and further oxidize the primary TBS using QFC (quinolinium fluoro-chromate, cf.: Murugensan, V.; Pandurangan, A. Ind. J. Chem. 1992, 31 (B), 377) preferentially in the presence of a secondary one. Unfortunately again, we failed to obtain any 36.
72. Sisler, H. H.; Audrieth, L. F. Inorg. Synth. 1946, 2, 173. It is noteworthy that using NaClO under phase transfer conditions (cf.: Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett. 1998, 39, 7263), PCC, Dess-Martin periodinane, or IBX gave substantially lower yields while Swern oxidation resulted in epimermization.
73. Sisler, H. H.; Audrieth, L. F. Inorg. Synth. 1946, 2, 173. It is noteworthy that using NaClO under phase transfer conditions (cf.: Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett. 1998, 39, 7263), PCC, Dess-Martin periodinane, or IBX gave substantially lower yields while Swern oxidation resulted in epimermization.
74. 42a and 42b (propane-1,3-dithol and bis-ethanethiol protected counterparts of 36) were synthesized from TBS ethers 40a/40b (derived from aldols 7c/7d) via alcohols 41a/41b. For structures and reaction details, see the Experimental Section in the Supporting Information.
75. Shi, X.-X.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 4331.
76. Use of proline ((a) Hojos, Z. C.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
77. (b) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395.) in our case led to no reaction at all, although it was quite effective on other substrates.
78. We only managed to find applications of this reaction to construction of seven-membered (see e.g.: (a) Kataoka, Y.; Nakamura, Y.; Morihira, K.; Arai, H. ; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1992, 33, 6979.
79. (b) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741) or larger (ref 44 below) rings in the literature.
80. Cockerill, G. S.; Kocienski, P.; Treadgold, R. J. Chem. Soc., Perkin Trans. 1 1985, 2093 and 2101.
81. Lorett, N. B.; Howard, W. L.; Brown, J. H. J. Org. Chem. 1959, 24, 1731.
82. Smith, A. B., III; Fukui, M.; Vaccaro, H. A.; Empfield, J. R. J. Am. Chem. Soc. 1991, 113, 2071.
83. Gemal, A. L.; Luche, J. L. J. Org. Chem. 1979, 44, 4187.
84. (a) Fujita, E.; Nagao, Y.; Kaneko, K. Chem. Pharm. Bull. 1978, 26, 3743.
85. (b) Lipshutz, B. H.; Moretti, R.; Crow, R. Tetrahedron Lett. 1989, 30, 15.
86. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553.
87. Shi, X.-X.; Wu, Q. Q. Synth. Commun. 2000, 30, 4081.
88. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
89. (b) De Munari, S.; Frigreio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272.
90. (c) Frigreio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
91. (a) Nicolaou, K. C.; Bunnage, M. E.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Agrios, K. A.; Gunzner, J. L.; Yang, Z. Chem. Eur. J. 1999, 5, 599.
92. (b) Russell, G. A.; Ochrymowy, L. A. J. Org. Chem. 1969, 34, 3618.
93. The stereogenic center at C-15 in this work was derived from a chiral epoxide of >99% ee (by chiral HPLC analysis) obtained by using Jacobsen HKR. For detailed information, see the Experimental Section, Part Two in the Supporting Information.
94. (a) Casy, G.; Gorins, G.; McCague, R.; Olivo, H. F.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 1085.
95. (b) Carnell, A. J.; Casy, G.; Gorins, G.; Kompany-Saeid, A.; McCague, R. ; Olivo, H. F.; Roberts, S. M.; Willets, A. J. Chem. Soc., Perkin Trans. 1 1994, 3431.
96. The yield for introduction of the BFA lower chain via a Michael addition was usually in the range of 70-80%. See: (a) Reference 13 above (80%).
97. (b) Baudouy, R.; Crabbé, P.; Greene, A. E.; Le Drian, C.; Orr, A. F. Tetrahedron Lett. 1977, 34, 2973 (82%).
98. (c) Köksal, Y.; Raddatz, P.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1980, 19, 472 (76%).
99. (d) Greene, A. E.; Le Drian, C.; Crabbé, P. J. Am. Chem. Soc. 1980, 102, 7584 (72%).
100. (e) Le Drian, C.; Greene, A. E. J. Am. Chem. Soc. 1982, 104, 5473 (72%).
101. (f) Corey, E. J.; Carpino, P. Tetrahedron Lett. 1990, 31, 7555 (72%).
102. (g) Nokami, J.; Ohkura, M.; Dan-Oh, Y.; Sakamoto, Y. Tetrahedron Lett. 1991, 32, 2409 (65%).
103. (h) Casy, G.; Gorins, G.; McCague, R.; Olivo, H. F.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 1085 (87%).
104. (i) Bernades, V.; Kann, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670 (89% or 76%).
105. See e.g.: (a) Reference 51.
106. (b) Reference 15a.
107. (c) Solladié, G.; Lohse, O. J. Org. Chem. 1993, 58, 4555.
108. (d) Nokami, J.; Ohkura, M.; Dan-Oh, Y.; Sakamoto, Y. Tetrahedron Lett. 1991, 32, 2409.
109. (e) Reference 55f.
110. (f) Troast, B. M.; Lynch, J.; Renault, P.; Steinman, H. J. Am. Chem. Soc. 1986, 108, 284.
111. Campbell, E. J.; Zhou, H.; Nguyen, S. T. Org. Lett. 2001, 3, 2391.
112. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
113. (b) For a review, see: Singh, V. K. Synthesis 1992, 605.
114. Liu, H.-J.; Yip, J.; Shia, K.-S. Tetrahedron Lett. 1997, 38, 2253.
115. Papadooulos, E. P.; Jarrar, A.; Issidorides, C. H. J. Org. Chem. 1966, 31, 615.
116. Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470.
117. Yamaguchi, M.; Innaga, J.; Hirata, K.; Saeki, H.; Katsuki, T. Bull. Chem. Soc. Jpn. 1979, 52, 1989.