Synthetic Studies on the Taxane Skeleton:Construction of Eight-Membered Carbocyclic Rings by the Intramolecular B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction

摘要

Construction of eight-membered carbocyclic rings via the intramolecular 6-alkyl Suzuki-Miyaura cross-coupling reaction has been studied.This protocol proved its potency through the formation of the eight-membered ring possessing a quaternary carbon on its ring in high yield,affording promise of a new access to the eight-membered ring of Taxol.Palladium-mediated cross-coupling reactions have been utilized in organic synthesis because of their high efficiency and mild conditions.Among these reactions,the most utilized C -C bond-forming cross-coupling reactions are Mizoroki-Heck,1 Stille,2 and Suzuki-Miyaura reactions.Because the Suzuki-Miyaura cross-coupling reaction is a powerful C-C bond-forming reaction under mild conditions,an increasing number of its variants have been reported.