Organic & Biomolecular Chemistry 2006-01-21

Enantioselective total syntheses of (-)-clasto-lactacystin beta-lactone and 7-epi-(-)-clasto-lactacystin beta-lactone.

Christopher J Hayes, Alexandra E Sherlock, Matthew D Selby

Index: Org. Biomol. Chem. 4(2) , 193-5, (2006)

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Abstract

An alkylidene carbene 1,5-CH insertion has been used as a key step in an efficient enantioselective total synthesis of (-)-clasto-lactacystin beta-lactone, and its C7-epimer. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.