SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .8. SYNTHESIS OF (+/-)-ARISTOLASICONE

被引：14

作者：

GULLER, R ^{[1
]}

DOBLER, M ^{[1
]}

BORSCHBERG, HJ ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM EIDGENOSS LAB,CH-8092 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 08期

关键词：

D O I：

10.1002/hlca.19910740804

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The revised structure of the indole alkaloid aristolasicone (2) was confirmed through a convergent total synthesis of the racemic form of this metabolite. The key step involves a one-pot condensation/cyclization reaction between 1-(4-methoxyphenylsulfonyl)-1H-indole-2-acetaldehyde (9) and (+/-)-trans-5-(2,6-difluorobenzyloxy)-p-menth-1-en-8-amine ((+/-)-7). The resulting allohobartine derivative (+/-)-13, obtained in 84% yield, was deprotected and oxidized to (+/-)-alloserratenone ((+/-)-15) which cyclized smoothly to the target molecule (+/-)-2 upon exposure to BF3.Et2O.

引用

页码：1636 / 1642

页数：7

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