1-Deoxy-5-hydroxysphingolipids as new anticancer principles: an efficient procedure for stereoselective syntheses of
John M Wiseman1, Frank E McDonald, Dennis C Liotta
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Abstract:
[reaction: see text]. Enantioselective preparation of the linear homoallylic alcohol I allows efficient formation of the 2-amino-3,5-diol moiety present in several biologically active compounds, including 1-deoxy-5-hydroxysphingosine analogue IV, which has exhibited excellent biological activity against colon cancer. The conversion of I into IV involves a sequence of enantioselective epoxidation of the O-tert-butoxycarbonyl derivative of I, followed by regioselective and stereospecific oxacyclization of II to introduce differentiated oxygens in III.
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