3-ALKYL 1,6-DIHYDROPYRIDINES FROM 3-ALKYL 5,6-DIHYDRO-PYRIDINIUM SALTS - IMPLICATIONS IN THE BIOSYNTHESIS OF SOME MACROCYCLIC MARINE ALKALOIDS

被引：26

作者：

GIL, L ^{[1
]}

GATEAUOLESKER, A ^{[1
]}

MARAZANO, C ^{[1
]}

DAS, BC ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 05期

关键词：

D O I：

10.1016/0040-4039(94)02339-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Additions of salts 1 and dihydropyridines 2 in an intramolecular manner have been invoked in the biosynthesis of some macrocyclic alkaloids such as manzamines, sarain A and halicyclamine A, recently isolated from sponges. We report conditions for the deprotonation of easily accessible salts 1, giving a regioselective entry to 3-alkyl 1,6-dihydropyridines 2. Also, we show that species 1 and 2 can be generated from a common intermediate such as 9. Dihydropyridines 2 are unstable at high temperatures giving isomeric 1,2- and 1,4-dihydropyridines, but were conveniently trapped by dienophiles to give synthetically useful isoquinuclidines such as 18 or 20.

引用

页码：707 / 710

页数：4

共 17 条

[1]

BALDWIN JE, 1992, TETRAHEDRON LETT, P2059

[2] FORMATION, STABILITY, AND PROTONATION OF DIHYDROPYRIDINES - MINDO-3 STUDY [J].