An asymmetric synthetic route to (+)-lactacystin

Abstract

Trihydroxy pyrrolidinone 16, a key intermediate to (+)-lactacystin 1, has been stereoselectively synthesized via the highly diastereoselective crotylboration of aldehyde 5 and intramolecular mercurioamidation of allylic trichloroacetimidate 12 to introduce the three requisite contiguous chiral centers of methyl, hydroxy and amino substituents.