Platinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated Enynes

Victor Mamane, Tobias Gress, Helga Krause and Alois Fürstner*

*Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany, Email: fuerstnermpi-muelheim.mpg.de

V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc., 2004, 126, 8654-8655.

DOI: 10.1021/ja048094q

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Abstract

Exposure of enynes containing a hydroxyl group at one of the propargylic positions to catalytic amounts of either PtCl₂ or (PPh₃)AuCl/AgSbF₆ results in a selective rearrangement with formation of bicyclo[3.1.0]hexan-3-one derivatives. A total synthesis of the terpenes sabinone and sabinol is described.

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see article for more reactions

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Key Words

Cyclopropanes, Cyclopentanones

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ID: J48-Y2004-1580