Stereospecific Formal Total Synthesis of Ecteinascidin 743

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 regiosel...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 45; no. 11; pp. 1754 - 1759
Main Authors:	Zheng, Shengping, Chan, Collin, Furuuchi, Takeshi, Wright, Benjamin J. D., Zhou, Bishan, Guo, Jinsong, Danishefsky, Samuel J.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 06-03-2006 WILEY‐VCH Verlag
Subjects:	Antineoplastic Agents, Alkylating - chemical synthesis Antineoplastic Agents, Alkylating - chemistry antitumor agents asymmetric synthesis Catalysis Dioxoles - chemical synthesis Dioxoles - chemistry Molecular Structure natural products Pictet-Spengler reaction Stereoisomerism Tetrahydroisoquinolines - chemical synthesis Tetrahydroisoquinolines - chemistry total synthesis
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Summary:	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.
Bibliography:	ark:/67375/WNG-LLMMHJKT-9 istex:F866D63742CB5C5BB8A73502B00D3A442E14A808 ArticleID:ANIE200503983 This work was supported by the National Institutes of Health (Grant HL25848) and by Pharmamar Corporation of Madrid, Spain. We thank Dr. Atsushi Endo for many helpful dicussions. B.J.D.W. gratefully acknowledges the NSF for a predoctoral fellowship. We thank Bristol Myers Squibb for the generous fellowship awarded to C.C. We also thank Dr. Yasuhiro Itagaki (Columbia University) for mass spectrometric analyses
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200503983