Stereospecific formal total synthesis of ecteinascidin 743

被引:95
作者
Zheng, SP [1 ]
Chan, C [1 ]
Furuuchi, T [1 ]
Wright, BJD [1 ]
Zhou, B [1 ]
Guo, J [1 ]
Danishefsky, S [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
antitumor agents; asymmetric synthesis; natural products; Pictet-Spengler reaction; total synthesis;
D O I
10.1002/anie.200503983
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A new strategy was designed for the construction of the pentacyclic ring system of ecteinascidin 743. Key features include highly concise routes to the enantiopure, configurationally matched subunit 1, a novel vinylogous Pictet-Spengler cyclization to 2, and a stereospecific epoxidation and regioselective reduction sequence of the C3-C4 enamide to secure 3. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1754 / 1759
页数:6
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