A novel enantioselective synthetic route to omuralide analogues with the potential for species selectivity in proteasome inhibition.
[reaction in text] The building blocks shown can be combined for an enantioselective construction of the simplified omuralide analogue 4 in nine steps, with the use of (R)-atrolactic acid as a recoverable chiral controller.
Crane
S N
SN
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D003546:Cysteine Endopeptidases / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D007773:Lactates / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors / Q000737:chemistry*; D046988:Proteasome Endopeptidase Complex; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007773:Lactates; D007783:Lactones; D009097:Multienzyme Complexes; C117645:omuralide; C067713:lactacystin; C005434:atrolactic acid; D003546:Cysteine Endopeptidases; D046988:Proteasome Endopeptidase Complex; D005998:Glycine; D000111:Acetylcysteine