1-Deoxy-5-hydroxysphingolipids as new anticancer principles: an efficient procedure for stereoselective syntheses of 2-amino-3,5-diols.
[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.
Wiseman
John M
JM
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
McDonald
Frank E
FE
Liotta
Dennis C
DC
D000438:Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D006028:Glycosphingolipids / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000970:Antineoplastic Agents; D006028:Glycosphingolipids