Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization

被引：29

作者：

Abelman, MM ^{[1
]}

Curtis, JK ^{[1
]}

James, DR ^{[1
]}

机构：

[1] Signature Biosci Inc, Richmond, CA 94804 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 34期

关键词：

indoles; N-acyliminium ion; erythrane; tryptamine; Pictet-Spengler;

D O I：

10.1016/S0040-4039(03)01190-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enaminoesters containing a tethered indole or aryl moiety on the amine react with substituted maleic anhydrides or acryloyl chlorides to provide pyrrolinone or dihydropyridone products, respectively. The indole-tethered dihydropyridones can be induced to undergo a one-pot cyclization whereas, the indole-tethered pyrrolinone intermediates are readily cyclized with HCl. The aryl-tethered pyrrolinones or dihydropyridones can be isolated and subsequently induced to cyclize with triflic acid. This methodology culminates in the synthesis of erythrane-like and other natural products that are readily amenable to combinatorial library production. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：6527 / 6531

页数：5

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