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Synfacts 2007(4): 0389-0389  
DOI: 10.1055/s-2007-968356
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ring Opening of a meso-Azabicyclic Alkene with an Arylboronic Acid

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
H. A. McManus, M. J. Fleming, M. Lautens*
University of Toronto, Canada
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The first enantioselective total synthesis of the biologically important (+)-homochelidonine was accomplished utilizing an excellent desymmetrization of a meso-bicylic alkene based on a palladium-catalyzed ring-opening reaction. This method creates two contiguous syn stereocenters from readily available meso compounds. Once this chirality is installed, subsequent diastereoselective bromohydrin formation leading to an epoxide is expertly accomplished.