Journal of the American Chemical Society, Vol.131, No.16, 5746-5746, 2009
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.