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Asymmetric Synthesis of (−)-Incarvillateine Employing an Intramolecular Alkylation via Rh-Catalyzed Olefinic C−H Bond Activation

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Andy S. Tsai, Robert G. Bergman and Jonathan A. Ellman

Department of Chemistry, University of California, Berkeley, California 94720

J. Am. Chem. Soc., 2008, 130 (20), pp 6316–6317

DOI: 10.1021/ja8012159

Publication Date (Web): April 29, 2008

Abstract

An asymmetric total synthesis of (−)-incarvillateine, a natural product having potent analgesic properties, has been achieved in 11 steps and 15.4% overall yield. The key step is a rhodium-catalyzed intramolecular alkylation of an olefinic C−H bond to set two stereocenters. Additionally, this transformation produces an exocyclic, tetrasubstituted alkene through which the bicyclic piperidine moiety can readily be accessed.

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Published In Issue May 21, 2008
Article ASAPApril 29, 2008
Received: February 18, 2008

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Communication

Asymmetric Synthesis of (−)-Incarvillateine Employing an Intramolecular Alkylation via Rh-Catalyzed Olefinic C−H Bond Activation

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Synthesis of (−)-Acutumine

Enantiospecific Total Syntheses of Kapakahines B and F

Stereoselective Alkylation of α,β-Unsaturated Imines via C−H Bond Activation

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