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
收藏
页码：8231 / 8234
页数：4
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