Total Synthesis of (±)-Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization

被引：42

作者：

Bajtos, Barbora ^{[1
]}

Pagenkopf, Brian L. ^{[1
]}

机构：

[1] Univ Western Ontario, Dept Chem, London, ON N6A 3K7, Canada

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Total synthesis; Natural products; Alkaloids; Nitrogen heterocycles; Cycloaddition; Donor-acceptor cyclopropane; Photocyclization; RING; ASPIDOSPERMINE; CYCLOPROPANES; QUEBRACHAMINE; DERIVATIVES; CYCLIZATION; SYSTEM;

D O I：

10.1002/ejoc.200801154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-quebrachamine has been completed in 13 linear steps and 17.8% overall yield. The indole core was constructed via a formal [3+2] dipolar cycloaddition between a functionalized nitrile and donor-acceptor cyclopropane, and the synthetically challenging nine-membered ring was secured by an efficient chloroacetamide photocyclization. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1072 / 1077

页数：6

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