Convergent Approach to the Tetracyclic Core of the Apparicine Class of Indole Alkaloids via a Key Intermolecular Nitrosoalkene Conjugate Addition

被引：9

作者：

Chauhan, Pradeep S. ^{[1
]}

Weinreb, Steven M. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

基金：

美国国家科学基金会;

关键词：

VINYLNITROSO COMPOUNDS; VALLESAMINE; (+/-)-ALSTILOBANINE; ALKYLATION; LEAVES;

D O I：

10.1021/jo501067u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available methyl 3-formylindol-2-ylacetate and N-tosyl-4-chloro-3-piperidone oxime have been used to construct the tetracyclic skeleton of the apparicine class of monoterpene indole alkaloids in only four steps in 80% overall yield. Key transformations in this convergent approach involve use of an intermolecular ester enolate/nitrosoalkene conjugate addition to form the C-15/16 bond, followed by a reductive cydization to construct the C-ring of the tetracycle.

引用

页码：6389 / 6393

页数：5