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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
journal contribution
posted on 1998-01-09, 00:00 authored by Qingbei Zeng, Simon Bailey, Ting-Zhong Wang, Leo A. PaquetteThe 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 13 to 14 is seen to be
unidirectional and consequently to offer useful potential
serviceability as more advanced thrusts toward Taxol are
mounted.