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 2006-03, Vol.45 (11), p.1754-1759
Main Authors: Zheng, Shengping, Chan, Collin, Furuuchi, Takeshi, Wright, Benjamin J. D., Zhou, Bishan, Guo, Jinsong, Danishefsky, Samuel J.
Format: Article
Language:English
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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503983