Catalytic Asymmetric Claisen Rearrangement in Natural Product Synthesis: Synthetic Studies toward (-)-Xeniolide F

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Org. Lett., 7 (25), 5705 -5708, 2005. 10.1021/ol052462t S1523-7060(05)02462-4
Web Release Date: November 17, 2005

Catalytic Asymmetric Claisen Rearrangement in Natural Product Synthesis: Synthetic Studies toward (-)-Xeniolide F

Annett Pollex and Martin Hiersemann*

Institut für Organische Chemie, Technische Universität Dresden, D-01062 Dresden, Germany

martin.hiersemann@chemie.tu-dresden.de

Received October 11, 2005

Abstract:

The catalytic asymmetric Claisen rearrangement (CAC) of a highly substituted and functionalized

-alkoxycarbonyl-substituted allyl vinyl ether has been exploited to gain access to an advanced building block for the projected total synthesis of (-)-xeniolide F, the enantiomer of a xenicane diterpene isolated from a coral of the genus Xenia.

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