Allylic Hydroxylation Through Acid Catalysed Epoxy Ring Opening of Betulinic Acid Derivatives

Abstract

Acid catalysed epoxy ring opening of several lupane type triterpenoids leads to unusual allylic hydroxylation. The reaction involves the formation of epoxide by m‐chloroperbenzoic acid followed by the treatment of mineral acid. The simple methodology finds utility to introduce a hydroxyl function at the allylic position in these triterpenoids, which is otherwise quite difficult.

Keywords:

• Betulinic acid derivatives
• allylic hydroxylation

Acknowledgment

The authors are thankful to the Director, Indian Institute of Chemical Biology, Kolkata, India for his keen interest in the work. One of the authors (S. P.) is grateful to Department of Biotechnology (DBT), New Delhi, India for providing a Junior Research Fellow (JRF).