title: Bicyclic Systems Related to Taxol. A Direct Means for Implementing C-2 Oxygenation and Demonstration of the Feasibility of alpha-Ketol Equilibration in a Fully Oxygenated B-Ring Setting.
abstract: The feasibility of alpha-ketol equilibration in a fully oxygenated B-ring setting for the rapid, enantioselective construction of an A/B bicyclic model related to Taxol has been examined. The key elements associated with this successful venture include selection of a proper array of protecting groups for the four hydroxyl groups present, suitable catalysis of the 1,2-pinacol-like shift, and an intrinsic dependence on the thermodynamic stabilities of the two alpha-ketol isomers. The key conversion of 13 to 14 is seen to be unidirectional and consequently to offer useful potential serviceability as more advanced thrusts toward Taxol are mounted.
authors.affiliation: Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210.
authors.forename: Qingbei
authors.initials: Q
authors.lastname: Zeng
authors.forename: Simon
authors.initials: S
authors.lastname: Bailey
authors.forename: Ting-Zhong
authors.initials: TZ
authors.lastname: Wang
authors.forename: Leo A.
authors.initials: LA
authors.lastname: Paquette