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.