Diastereoselective synthesis of scyphostatin and analogs

ORGN 699

Yaodong Huang, yhuang@chem.ucsb.edu and Thomas R. R. Pettus, pettus@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93117
A new efficient method for the synthesis of scyphostatin and its analogs is presented. Starting from 2,4-dihydroxy benzylaldehyde, an advanced tyrosine analog enantioselectively prepared in 6 steps. Distereoselective cyclization of the tyrosine analog with PIFA followed by selective epoxidization give the core of scyphostatin. A sorbic acid derivative is prepared.