Catalyst-Directed Diastereoselective Isomerization of Allylic Alcohols

Steroids are characterized by a prototypical cyclopenteno-phenanthrene ring system and a side chain attached to this polycyclic framework at C17. Driven by the distinguished biological activity differences between C20-(R) and C20-(S) isomers, the specific stereocontrolled construction of this exo-cyclic stereocenter is recognized as one of the most difficult challenges in the field. The group of Professor Clément Mazet at the University of Geneva (Switzerland) has recently reported a stereospecific catalytic strategy for the perfectly stereocontrolled installation of C20, using a catalyst-directed diastereoselective isomerization of allylic alcohols.

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