TOTAL SYNTHESIS OF (+/-)-7-EPI-20-DESETHYLGELSEDINE

被引：26

作者：

KENDE, AS

LUZZIO, MJ

MENDOZA, JS

机构：

[1] Department of Chemistry, University of Rochester, Rochester

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 03期

关键词：

D O I：

10.1021/jo00290a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxindole alkaloid gelsedine contains a unique molecular architecture. The synthetic approach to this pentacyclic molecule involved the efficient preparation of the all-cis trisubstituted pyrrolidine intermediate 14. The lactone system 18, an excellent precursor of the pentacyclic cage framework of gelsedine, was prepared in an efficient and highly convergent manner by reaction of pyrrolidine 16 and the readily available N-methoxyindole system 5. Subsequent steps led to the formation of the title compound. © 1990, American Chemical Society. All rights reserved.

引用

页码：918 / 924

页数：7

共 19 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].