Title, Authors, Journal name: An Efficient, Stereocontrolled Synthesis of a Potent Omuralide-Salinosporin Hybrid for Selective Proteasome Inhibition. Reddy, Leleti Rajender; Fournier, Jean-Francois; Reddy, B. V. Subba; Corey, E. J.. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA. Journal of the American Chemical Society (2005), 127(25), 8974-8976.

Abstract: A short and highly stereocontrolled synthesis of the potent proteasome inhibitor I (antiprotealide) from the (S)-threonine-derived oxazoline II has been developed. The key steps include a diastereoselective aldol coupling, an internal carbo-titanation using Kulinkovich reagent, diastereoselective cyclization, and demethylation with [Me2AlTeMe]2. The potency of I against the .beta.5-subunit of human 20S proteasome was about 2.5 times that of omuralide.