Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline

被引：72

作者：

Overman, LE ^{[1
]}

Peterson, EA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 22期

关键词：

alkaloids; alkylation; asymmetric catalysis; C-C coupling; Heck reaction;

D O I：

10.1002/anie.200351260

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereogenic quaternary carbons present the primary challenge in the syntheses of trispyrrolidinoindoline alkaloids such as idiospermuline. In its synthesis the two contiguous quaternary centers are expediently addressed by combining the lithium dienolate of a differentially protected dihydroisoindigo with a tartrate-derived electrophile. The third quaternary stereocenter is introduced by a catalytic asymmetric Heck reaction.

引用

页码：2525 / 2528

页数：4

共 23 条

[1]

Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9

[2] SYNTHESIS AND STEREOCHEMISTRY OF SOME ISATYLIDENEACETIC ACID DERIVATIVES [J].