Synthesis of aspidospermidine alkaloids from 1,2,3,4-tetrahydrocarbazole:: Total stereoselective synthesis of (±)-18-noraspidoshermidine.

被引：35

作者：

Urrutia, A ^{[1
]}

Rodríguez, JG ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 36期

关键词：

(+/-)-18-noraspidospermidine; tetrahydrocarbazolones; nickel boride; stereoselective reduction; indolisation;

D O I：

10.1016/S0040-4020(99)00614-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of the 1,2,3,4-tecrahydrocarbazol-4-one derivatives has been analysed and applied to the synthesis of (+/-)-18-noraspidospermidine (1b). This was synthesised, starting from 4-(1'3'-dioxolan-2'-yl)cyclohexanone which was successively transformed to 3-methyl-3-(3'-nitropropyl)-1,2,3,4-tetrahydrocarbazol-4-one and to the imine tetracycle 13 by means of nickel boride catalyst. The reduction of 13 to the natural cis D ring junction was carried out with the LiAlH4/AlCl3 system. The construction of the E-ring was carried out by a Pummerer type reaction from thecis-7-tosyl-1-phenylthioacetamide derivative 17 by oxidation followed by intramolecular cyclisation, desulfurization and reduction to 1b. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11095 / 11108

页数：14

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