Stereoselective preparation of the ABCD tetracycle of the 20-methyl analogue of aspidospermidine and related alkaloids.

被引：10

作者：

Urrutia, A ^{[1
]}

Rodríguez, JG ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 23期

关键词：

aspidospermidine; Henry reaction; indolisation; nickel boride;

D O I：

10.1016/S0040-4039(98)00710-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural cis[ABCD] tetracycle of the 20-methyl analogue of aspidospermidine has been synthesised, starting from the 4,4-ethylenedioxy-1-cyclohexanone. This, was transformed into 3-methyl-3-(3'-nitropropyl)-1,2,3,4-tetrahydrocarbazol-4-one. Two key synthetic steps permits the construction of the D ring: i) the one pot nickel boride catalyst to the imine tetracycle in excellent yield; and ii) the stereoselective reduction of this imine to the natural cis D ring junction in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4143 / 4146

页数：4

共 9 条

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