Eric Tisdale - Unified synthesis of caged Garcinia natural products based on a site‐selective Claisen/Diels–Alder/Claisen rearrangement.

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  Tisdale, E. J.; Slobodov, I.; Theodorakis, E. A. Unified   synthesis of caged Garcinia natural products based on a   site‐selective Claisen/Diels-Alder/Claisen rearrangement.   Proc. Natl. Acad. Sci. U.S.A. 2004,   101, 12030-12035.


    A unified synthetic strategy toward caged   Garcinia   natural products has been designed and implemented. Central to   the strategy is a tandem Claisen/Diels-Alder/Claisen   rearrangement of a suitably substituted xanthone precursor to   form forbesione. Serving as a template, forbesione is then used   to deliver representative members of this family, including   desoxygaudichaudione A, desoxymorellin, and gambogin. Studies on   the timing of this reaction cascade suggest that the C-ring   Claisen/Diels-Alder rearrangement proceeds initially and is   followed by the A-ring Claisen reaction. The electronic and   steric effects that govern the outcome of this cascade are   presented.

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