A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity

EJ Corey, W Li, GA Reichard

Index: Corey; Li, Weidong; Reichard, Gregory A. Journal of the American Chemical Society, 1998 , vol. 120, # 10 p. 2330 - 2336

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Citation Number: 96

Abstract

A new process is described for metal-catalyzed doubly diastereoselective Mukaiyama aldol coupling of a chiral tertiary α-amino aldehyde and an achiral silyl enol ether to form selectively an anti-aldol product. The metal requirement is strict, since of several salts tested only MgI2 functions as an effective catalyst. The MgI2-catalyzed aldol greatly facilitates the total synthesis of lactacystin (1) and the corresponding β-lactone (2), microbial products ...