ORGN 263 |
| We have prepared both antipodes of 3-adeninyl-5-hydroxymethyl-2-pyrrolidone and of 3-guanidinyl-5-hydroxymethyl-2-pyrrolidine via two synthetic routes. The first converts either (R)- or (S)-glutamic acid to a chiral bicyclic oxazolidine. Subsequent MoOPh oxidation and eventual Mitsunobu coupling with adenine or protected guanine leads to the target, after deprotection. The second route begins with hydroxyproline, also converted to the key oxazolidine by ruthenium-catalyzed oxidation to the lactam. Mitsunobu coupling leads to both adenine and guanine derivatives. In both routes, and for all targets, stereochemical integrity is retained throughout the synthetic scheme. These compounds are being tested for anti-viral activity, as well as for anti-bacterial activity. |
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Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Monday, 14 March 2005 Convention Center -- Room 11A, Oral
Division of Organic Chemistry |
