Eric Tisdale - Caged natural products of Garcinia trees: Total synthesis of forbesione, desoxymorellin, gambogin, desoxygaudichaudione A, and seco-lateriflorone.

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  Tisdale, E. J. Caged natural products of Garcinia trees: Total   synthesis of forbesione, desoxymorellin, gambogin,   desoxygaudichaudione A, and seco-lateriflorone. Ph.D. Thesis,   University of California, San Diego, 2004.


  The work presented herein is the culmination of synthetic studies   in the area of caged Garcinia natural products,   compounds that have been targeted synthetically since their   structural elucidation, and compounds found in a variety of   Garcinia tree products from folk medicines to pigments.   This treatise on the synthesis of caged natural products of the   Garcinia is divided into six parts: (1) an introduction   describing the caged natural products of Garcinia trees   along with their rich history; (2) model studies on the tandem   Claisen/Diels-Alder rearrangement leading to a successful   synthesis of the caged unit that defines this class of natural   products; (3) an investigation into the preparation of the   xanthone backbone of these caged xanthonoids, studies culminating   in the total synthesis of atroviridin, a related xanthone natural   product; (4) the application of the xanthone and tandem   Claisen/Diels-Alder rearrangement studies to the total synthesis   of forbesione--the simplest of the caged xanthonoids--and its use   as a structural base for the synthesis of more complex   structures; (5) the total synthesis of the rearranged caged   xanthonoid, seco -lateriflorone; (6) and concluding remarks. The   tandem Claisen/Diels-Alder and Claisen/Diels-Alder/Claisen   rearrangements, the reactions responsible for the generation of   the elusive caged structure and forbesione-type natural products   respectively, are central to this work and are discussed in   detail--in regard to their timing, selectivity, and their role in   nature--with pertinent synthetic studies where it is merited.

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