Total synthesis of haliclamine A, a macrocyclic marine alkaloid related to the key biogenetic intermediate of manzamines

作者: Yoshiki Morimoto , Chiho Yokoe

DOI: 10.1016/S0040-4039(97)10368-9

关键词:

摘要: Abstract The first total synthesis of haliclamine A (1), a macrocyclic marine alkaloid closely related to the key bisdihydropyridine intermediate 3 biogenetically unique manzamine family, has been efficiently achieved via stepwise inter- and intramolecular N-alkylations 3-alkylpyridine derivatives 26 28.

参考文章(22)
Jack E Baldwin, Tim D.W Claridge, Andrew J Culshaw, Florian A Heupel, Svatava Smrcková, Roger C Whitehead, A biomimetic approach to the manzamine alkaloids Tetrahedron Letters. ,vol. 37, pp. 6919- 6922 ,(1996) , 10.1016/0040-4039(96)01516-X
Yasuhiro Torisawa, Akihiro Hashimoto, Masako Nakagawa, Hiroko Seki, Ritsuko Hara, Tohru Hino, A total synthesis of manzamine C and its geometrical isomer Tetrahedron. ,vol. 47, pp. 8067- 8078 ,(1991) , 10.1016/S0040-4020(01)91003-8
Bill J. Baker, Paul J. Scheuer, James N. Shoolery, Papuamine, an antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp Journal of the American Chemical Society. ,vol. 110, pp. 965- 966 ,(1988) , 10.1021/JA00211A046
N. Fusetani, K. Yasumuro, S. Matsunaga, H. Hirota, Haliclamines A and B, cytotoxic macrocyclic alkaloids from a sponge of the genus Haliclona Tetrahedron Letters. ,vol. 30, pp. 6891- 6894 ,(1989) , 10.1016/S0040-4039(01)93381-7
Ryuichi Sakai, Shigeo Kohmoto, Tatsuo Higa, Charles W. Jefford, Gérald Bernardinelli, Manzamine B and C, two novel alkaloids from the sponge haliclona sp. Tetrahedron Letters. ,vol. 28, pp. 5493- 5496 ,(1987) , 10.1016/S0040-4039(00)96762-5
Laurent Gil, Alice Gateau-Olesker, Christian Marazano, Bhupesh C. Das, 3-Alkyl 1,6-dihydropyridines from 3-alkyl 5,6-dihydro-pyridinium salts. Implications in the biosynthesis of some macrocyclic marine alkaloids Tetrahedron Letters. ,vol. 36, pp. 707- 710 ,(1995) , 10.1016/0040-4039(94)02339-D
Michael T. Davies-Coleman, D. John Faulkner, Gene M. Dubowchik, Gregory P. Roth, Craig Polson, Craig Fairchild, A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa Journal of Organic Chemistry. ,vol. 58, pp. 5925- 5930 ,(1993) , 10.1021/JO00074A017
Jack E. Baldwin, Tim D.W. Claridge, Florian A. Heupel, Roger C. Whitehead, A biomimetic approach to the manzamine alkaloids; model studies Tetrahedron Letters. ,vol. 35, pp. 7829- 7832 ,(1994) , 10.1016/0040-4039(94)80129-0
Eoin Fahy, Tadeusz F. Molinski, Mary Kay Harper, Brian W. Sullivan, D.John Faulkner, Laszlo Parkanyi, Jon Clardy, Haliclonadiamine, an antimicrobial alkaloid from the sponge Haliclona sp. Tetrahedron Letters. ,vol. 29, pp. 3427- 3428 ,(1988) , 10.1016/0040-4039(88)85180-3