Publication Details (including relevant citation information):
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.
Address (URL): http://goo.gl/hnDte