An enantiocontrolled synthesis of a key intermediate to (+)-lactacystin

Abstract
An asymmetric synthesis of a key intermediate 16 to (+)-lactacystin 1 has been established starting from epoxide 2 via intramolecular mercurioamidation of allylic trichloroacetimidate 4 and concomitant addition-reduction of ester 13 by Pri MgBr, in which reduction of the intermediate ketone proceeded with complete stereoselectivity.

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