Total synthesis and stereochemistry of cytoblastin

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8180-8181

  Moreno, Ofir A ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOBLASTIN; IMMUNOMODULATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029832318     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9618412     Document Type: Article

References (28)

1. Kumagai, H.; lijima, M.; Dobashi, K.; Naganawa, H.; Sawa, T.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 1029-1032.
2. Fujiki, H.; Suganuma, M.; Tahira, T.; Yoshioka, A.; Nakayasu, M.; Endo, Y.; Shudo, K.; Takayama, S.; Moore, R. E.; Sugimura, T. Cellular Interactions by Environmental Tumor Promoters; Japan Scientific Societies Press: Utrecht, 1984; pp 37-45.
3. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
4. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
5. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
6. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
7. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
8. For some recent activities in this area, see: Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924. Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc: 1995, 117, 6666-6672. Irie, K.: Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855. Endo, Y.; Yamaguchi, M.; Hirano, M.; Shudo, K. Chem. Pharm. Bull. 1996, 44, 1138-1149. Sugita, K.; Sawada, D.; Sodeoka, M.; Sasai, H.; Shibasaki, M. Chem. Pharm. Bull. 1996, 44, 463-465.
9. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676. For a review on this work, see: Rando, R. R.; Kishi, Y. Biochemistry 1992, 31, 2211-2218.
10. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676. For a review on this work, see: Rando, R. R.; Kishi, Y. Biochemistry 1992, 31, 2211-2218.
11. 1 is adopted in this paper.
12. Endo, Y.; Hasegawa, M.; Itai, A.; Shudo, K.; Tori, M.; Asakawa, Y.; Sakai, S. Tetrahedron Lett. 1985, 26, 1069-1072.
13. Although 2 can be purchased at considerable expense, it is readily prepared via published protocols, e.g.: Kogan, T. P.; Somers, T. C.; Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
14. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301-302.
15. Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343-3346.
16. Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735.
17. Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099-2102.
18. Fujii, N.; Futaki, S.; Yasamura, K.; Yajima, H. Chem. Pharm. Bull. 1984, 32, 2660-2665.
19. Hannon, S. T.; Traylor, T. G. J. Chem. Soc., Chem. Commun. 1975, 630-631.
20. 1H NMR). The analogous trans-allylstannane was prepared via conjugate addition of Lipshutz's mixed higher order stannylcuprate (Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065-2068) to the allylic acetate derived from the same protected formylindole; this longer sequence was forsaken, as the two allylstannanes produced degenerate results in the subsequent coupling.
21. Multivariable and mechanistic analyses of the reaction pathway will be given in detail: Moreno, O. A. Ph.D. Dissertation. Harvard University, 1996.
22. Muchowski, J. M.; Solas, D. R. J. Org. Chem. 1984, 49, 203-205.
23. We are indebted to Drs. Kumagai and Naganawa at Microbial Chemistry Research Foundation for a sample of natural cytoblastin.
24. Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
25. 1H NMR and diagnostic NOEs of the two indolactam V conformations, see ref 5.
26. For the details, see the 2D COSY and NOESY spectra included in the supporting information.
27. MacroModel version 4.5 provided courtesy of Prof. Still, Columbia University. Minimizations were performed on a Silicon Graphics Indigo workstation.
28. Assays performed by Prof. Rando at Harvard Medical School and by Dr. Gusovsky at Eisai Research Institute. Details of these assays are published elsewhere.