10.1021/jo971592f.s001 Qingbei Zeng Qingbei Zeng Simon Bailey Simon Bailey Ting-Zhong Wang Ting-Zhong Wang Leo A. Paquette Leo A. Paquette Bicyclic Systems Related to Taxol. A Direct Means for Implementing C-2 Oxygenation and Demonstration of the Feasibility of α-Ketol Equilibration in a Fully Oxygenated B-Ring Setting American Chemical Society 1998 Bicyclic Systems Related ketol Direct Means Taxol hydroxyl groups enantioselective construction 1998-01-09 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Bicyclic_Systems_Related_to_Taxol_A_Direct_Means_for_Implementing_C-2_Oxygenation_and_Demonstration_of_the_Feasibility_of_-Ketol_Equilibration_in_a_Fully_Oxygenated_B-Ring_Setting/3708180 The feasibility of α-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 α-ketol isomers. The key conversion of <b>13</b> to <b>14</b> is seen to be unidirectional and consequently to offer useful potential serviceability as more advanced thrusts toward Taxol are mounted.