Total syntheses of macrocyclic marine alkaloids, haliclamines A and B: A convenient and expeditious assembly of 3-substituted pyridine derivatives with different alkyl chains to the bispyridinium macrocycle

被引:24
作者
Morimoto, Y [1 ]
Yokoe, C [1 ]
Kurihara, H [1 ]
Kinoshita, T [1 ]
机构
[1] Osaka City Univ, Dept Chem, Grad Sch Sci, Osaka 5588585, Japan
关键词
D O I
10.1016/S0040-4020(98)00752-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total syntheses of haliclamines A (1) and B (2), macrocyclic marine alkaloids closely related to the key bisdihydropyridine intermediate 3 of the biogenetically unique manzamine family, have efficiently been achieved via stepwise controlled inter- and intramolecular N-alkylations of 3-alkylpyridine derivatives such as 40 and 41. The general synthetic methodology toward the bispyridinium macrocycle 44, a key biogenetic equivalent of the polycyclic marine alkaloids, has been proposed through the total syntheses. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12197 / 12214
页数:18
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