Cyclization reactions of N-acryloyl-2-aminobenzaldehyde derivatives:: formal total synthesis of martinellic acid

被引：31

作者：

He, Yong ^{[1
]}

Mahmud, Hossen ^{[1
]}

Moningka, Remond ^{[1
]}

Lovely, Carl J. ^{[1
]}

Dias, H. V. Rasika ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 37期

关键词：

D O I：

10.1016/j.tet.2006.06.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Alkyl acryloylamides derived from o-aminobenzaldehyde derivatives react with N-alkyl glycine derivatives to provide cis-fused pyrrole[3,2-c]quinolones in moderate yield and high diastereoselectivity. These same substrates engage in a tandem Michael-Mannich pathway on treatment with a secondary amine, providing corresponding quinolone derivatives. The elaboration of a pyrroloquinolone derivative via addition of an in situ generated functionalized copper acetylide to an in situ generated iminium ion provided the C2-substituted derivative. Global deprotection and reduction of the alkyne afford the tricyclic triamine core (as the HCl salt) found in martinellic acid. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8755 / 8769

页数：15

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