A short and efficient synthesis of (-)-7-methylomuralide, a potent proteasome inhibitor.
Short, practical, and scalable syntheses of (+/-)-7-methylomuralide and (-)-7-methylomuralide have been developed. Three consecutive tandem reaction pairs establish all of the carbons and the stereochemistry of the target molecule, vastly simplifying the synthetic scheme from N-trichloroethoxycarbonyl glycine. The chiral directing group controls the absolute stereochemistry of the key aldol reaction.
Shenvi
Ryan A
RA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ