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Photochemical Benzannulation Applied to the Total Synthesis of Hybocarpone and Hamigerans

David Lawrence Firman Gray

出版	Scripps Research Institute, La Jolla, California, 2003
URL	http://books.google.com.hk/books?id=TsFStwAACAAJ&hl=&source=gbs_api

註釋

A number of naturally occurring substances contain ring systems which are fused to an aromatic nucleus. A general and streamlined method for the construction of certain benzannulated bi- and polycyclic carbon frameworks has been investigated and its scope and limitations described. This method, based upon the photochemical generation and subsequent Diels-Alder trapping of hydroxy- o -quinodimethanes, was optimized to set the stage for the total synthesis of hybocarpone and the hamigerans. The synthetic route to hybocarpone features a radical-based dimerization event which may not be too dissimilar to the pathway adopted by nature for its construction. The intramolecular trapping of photo-generated hydroxy-o-quinodimethanes was the centerpiece in a successful asymmetric synthesis of several members of the hamigeran family including hamigerans A and B.