Formal synthesis of Manzamine C via a sila-Cope elimination

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 5959-5966

  Vidal, Thierry ^a   Magnier, Emmanuel ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYTOTOXIC AGENT; MANZAMINE C; NATURAL PRODUCT; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MARINE ENVIRONMENT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 0032575221     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00270-1     Document Type: Article

References (19)

1. 1) a) Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc. 1986, 108, 6404-6405.
2. b) Sakai, R.; Kohmoto, S.; Higa, T.; Jefford, C. W.; Bernardinelli, G. Tetrahedron Lett. 1987, 28, 5493-5496.
3. c) Nakamura, H.; Deng, S.; Kobayachi, J.; Ohizumi, Y.; Tomotake, Y.; Matsuzaki, T. Tetrahedron Lett. 1987, 28, 621-624.
4. d) Ichiba, T.; Sakai, R.; Kotmoto, S.; Saucy, G.; Higa, T. Tetrahedron Lett. 1988, 29, 3083-3086.
5. e) Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sakai, T.; Kobayashi, J; J. Org. Chem. 1992, 57, 2480-2483.
6. f) Ichiba, I; Corgiat, J. M.; Scheuer, P. J.; Borges, M. K. J. Nat. Prod. 1994, 57, 168-170.
7. g) Tsuda, M.; Kawasaki, N.; Kobayashi, J. Tetrahedron Lett. 1994, 35, 4387-4388.
8. h) Kobayashi, M.; Chen Y.-J.; Aoki, S.; In, Y.; Ishida, T.; Kitagawa, I. Tetrahedron, 1995, 51, 3727-3736.
9. 2) a) Magnier, E.; Langlois, Y.; Merienne, C. Tetrahedron Lett. 1995, 36, 9475-9478 and references there in.
10. b) Baker, B.J. b-Carboline and Isoquinoline Alkaloids from Marine Organisms. In Pelletier S.W. Alkaloids: Chemical and Biological Perspective, 1996, 10, 358-407
11. 3) Torisawa, Y.; Hashimoto, A.; Nakagawa, M.; Seki, H.; Hara, R.; Hino, T. Tetrahedron, 1991, 38, 8067-8078.
12. 4) Nowak, W.; Gerlach, H. Liebigs Ann. Chem. 1993, 153-159.
13. 5) Torisawa, Y.; Hashimoto, A.; Okouchi, M.; Iimori, T.; Nagasawa, M.; Hino, T.; Nakagawa, M. Bioorg. Med. Chem. Lett. 1996, 6, 2565-2570.
14. 6) Bac, N. V.; Langlois, Y. J. Am. Chem. Soc. 1982, 104, 7666-7667.
15. 7) Nyström, J.-E.; McCanna, T. D.; Helquist, P.; Amouroux, R. Synthesis, 1988, 56-58.
16. 8) Nagai, M.; Gaudino, J.J.; Wilcox, C.S. Synthesis, 1992, 163-168.
17. 9) Langlois, Y.; Konopski, L.; Bac, N. V.; Chiaroni, A.; Riche. C. Tetrahedron Lett. 1990, 31, 1865-1868 and Tetrahedron Lett. 1990, 31, 6450.
18. 9) Langlois, Y.; Konopski, L.; Bac, N. V.; Chiaroni, A.; Riche. C. Tetrahedron Lett. 1990, 31, 1865-1868 and Tetrahedron Lett. 1990, 31, 6450.
19. 10) During a tentative separation of diastereomeric N-oxides 8 and 9 by chromatography on silica gel, it was observed that N-oxide 9 decomposed spontaneously affording 11, whereas N-oxide 8 was more stable and gave rise to the expected elimination product 10 after heating in acetonitrile.