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Org. Biomol. Chem., 2006, 4, 193 - 195, DOI: 10.1039/b516311k

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

Christopher J. Hayes, Alexandra E. Sherlock and Matthew D. Selby

An alkylidene carbene 1,5-CH insertion has been used as a key step in an efficient enantioselective total synthesis of (–)-clasto-lactacystin -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.

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