Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin.
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.
Hayes
Christopher J
CJ
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK. chris.hayes@nottingham.ac.uk
Sherlock
Alexandra E
AE
Green
Martin P
MP
Wilson
Claire
C
Blake
Alexander J
AJ
Selby
Matthew D
MD
Prodger
Jeremy C
JC
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
D000900:Anti-Bacterial Agents; D007783:Lactones; C117645:omuralide; C067713:lactacystin; D000111:Acetylcysteine