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.

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