Total Synthesis of (±)-Aspidophylline A

被引：87

作者：

Ren, Weiwu ^{[1
]}

Wang, Qian ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Synth & Nat Prod, EPFL SB ISIC LSPN, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 07期

基金：

瑞士国家科学基金会;

关键词：

bridged ring systems; intramolecular Michael addition; monoterpene indole alkaloids; quaternary carbon atoms; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; INTRAMOLECULAR CONJUGATE ADDITION; ENANTIOSPECIFIC TOTAL-SYNTHESIS; INDOLE ALKALOIDS; GENERAL-APPROACH; STRYCHNOS ALKALOIDS; AKUAMMILINE; CYCLIZATION; CONSTRUCTION;

D O I：

10.1002/anie.201310929

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of aspidophyllineA, a pentacyclic akuammiline-type monoterpene indole alkaloid, is described. The synthesis features: 1)rapid access to a fully functionalized dihydrocarbazole through the desymmetrization of readily available 2-allyl-2-(o-nitrophenyl)cyclohexane-1,3-dione; 2)an intramolecular azidoalkoxylation of an enecarbamate to install both the furoindoline ring and the azido functionality; and 3)an intramolecular Michael addition for the construction of the 2-azabicyclo[3.3.1]nonane ring system.

引用

页码：1818 / 1821

页数：4

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