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Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

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Phil S. Baran* and Jeremy M. Richter

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037

J. Am. Chem. Soc., 2005, 127 (44), pp 15394–15396

DOI: 10.1021/ja056171r

Publication Date (Web): October 18, 2005

Abstract

The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole−carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.

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Published In Issue November 09, 2005
Received September 8, 2005

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Communication

Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

Abstract

Available Supporting Information for This Article

Crystallographic Information File

PDF

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History

Recommend & Share

Related Content

Direct Coupling of Indoles with Carbonyl Compounds: Short, Enantioselective, Gram-Scale Synthetic Entry into the Hapalindole and Fischerindole Alkaloid Families

Total Synthesis of Vinigrol

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

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