ORGN 152 |
| Chiral C2- and C3-functionalized aldono-1,4-lactone derivatives derived from L-ascorbic acid can be valuable intermediates in the synthesis of pharmacologically active agents. The synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-L-galactono-γ-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-L-galactono-γ-lactone derivatives can be accomplished from the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-L-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. In addition, 2-alkyl-3-amino and 3-alkyl-2-amino-L-galactono-γ-lactones are also synthesized from reductive amination of the C3- and C2-keto groups of the aforementioned isopropylidene derivatives of ascorbic acid. |
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |