Modular total synthesis of lamellarin D

被引：110

作者：

Pla, D ^{[1
]}

Marchal, A ^{[1
]}

Olsen, CA ^{[1
]}

Albericio, F ^{[1
]}

Alvarez, M ^{[1
]}

机构：

[1] Univ Barcelona, Biomed Res Inst, E-08028 Barcelona, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 20期

关键词：

D O I：

10.1021/jo051083a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).

引用

页码：8231 / 8234

页数：4

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