Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure

• Isomerization of epoxides on TiO2.
• Synthesis of bicyclic non-isomerized allylic alcohols.
• Potent anti-Parkinson activity.
• Cyclopentene type products over Au/TiO2.

A novel method of (1S,2R,3R,5R)-6,6-dimethyl-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene α-hydroxy ketone.

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