title: Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin.
abstract: An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. 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.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK. chris.hayes@nottingham.ac.uk
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Hayes
authors.forename: Alexandra E
authors.initials: AE
authors.lastname: Sherlock
authors.forename: Martin P
authors.initials: MP
authors.lastname: Green
authors.forename: Claire
authors.initials: C
authors.lastname: Wilson
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Blake
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Selby
authors.forename: Jeremy C
authors.initials: JC
authors.lastname: Prodger
mesh_terms: D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D007783:Lactones; C117645:omuralide; C067713:lactacystin; D000111:Acetylcysteine