Short synthesis of (+/-)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine

被引：23

作者：

Lounasmaa, M

Miettinen, J

Hanhinen, P

Jokela, R

机构：

[1] Lab. for Organ./Bioorg. Chemistry, Technical University of Helsinki

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(97)00056-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of 3-ethylindolo[2,3-a]quinolizidine 4a (regenerated from the corresponding alpha-aminonitrile 4b) afforded enamine 5. Catalytic hydrogenation of compound 5, led stereoselectively to compound 6 (pseudo), which is the highly desired intermediate for the preparation of several Corynanthe alkaloids, including (+/-)-hirsutine 7. (C) 1997 Elsevier Science Ltd.

引用

页码：1455 / 1458

页数：4

共 15 条

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