Enantioselective total syntheses of (-)-clasto-lactacystin beta-lactone and 7-epi-(-)-clasto-lactacystin beta-lactone.
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.
Hayes
Christopher J
CJ
School of Chemistry, University of Nottingham, University Park, Nottingham, UKNG7 2RD.
Sherlock
Alexandra E
AE
Selby
Matthew D
MD
D000438:Alcohols; D001565:Benzoates; D001597:Benzylidene Compounds; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis; D007783:Lactones / Q000138:chemical synthesis*; D008722:Methods; D013237:Stereoisomerism
D000438:Alcohols; D001565:Benzoates; D001597:Benzylidene Compounds; D015853:Cysteine Proteinase Inhibitors; D007783:Lactones; C098869:clasto-lactacystin beta-lactone