Title, Authors, Journal name: A Simple Stereocontrolled Synthesis of Salinosporamide A. Reddy, Leleti Rajender; Saravanan, P.; Corey, E. J.. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA. Journal of the American Chemical Society (2004), 126(20), 6230-6231.

Abstract: A simple and effective stereocontrolled synthesis of salinosporamide A has been developed. Of special note is the direct conversion of amino(benzyloxymethyl)hydroxybutanoate I (R = H) to acryloyl deriv. I (R = COCH:CH2). Also, quinuclidine proved to be superior to other bases in the cyclization of oxybutanoate II to oxopyrrolidinecarboxylate III. This process, the first synthesis of salinosporamide A, is capable of providing the compd. in substantial quantities for further biol. studies. Salinosporamide A was of special interest as a synthetic target because of its potent in vitro cytotoxic activity against many tumor cell lines (IC50 values of 10 nM or less).