1027180-03-5

Upstream product

• 200704-89-8 (E)-(1S,2R,3S)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol 
• 200704-88-7 (E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one 
• 200704-99-0 (E)-(6S,7R,8S)-7-(4-Methoxy-benzyloxy)-6-(2-methoxy-ethoxymethoxy)-5,5,11,11-tetramethyl-bicyclo[6.2.1]undec-1-ene 
• 200704-91-2 (1S,6S,7R,8S)-1-Hydroxy-7-(4-methoxy-benzyloxy)-6-(2-methoxy-ethoxymethoxy)-5,5,11,11-tetramethyl-bicyclo[6.2.1]undecan-2-one 
• 200704-90-1 (1S,2S,6S,7R,8S)-7-(4-Methoxy-benzyloxy)-6-(2-methoxy-ethoxymethoxy)-5,5,11,11-tetramethyl-bicyclo[6.2.1]undecane-1,2-diol 
• 200705-00-6 (1S,6S,7R,8S)-7-(4-Methoxy-benzyloxy)-6-(2-methoxy-ethoxymethoxy)-5,5,11,11-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-bicyclo[6.2.1]undecan-2-one 

Relevant academic research and scientific papers

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

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 13 to 14 is seen to be unidirectional and consequently to offer useful potential serviceability as more advanced thrusts toward Taxol are mounted.