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ChemInform Abstract: A Novel Entry to Naturally Occurring 5-Alkenyl α,β-Unsaturated δ-Lactones from D-Glucose: Syntheses of (+)-Acetylphomalactone and (+)-Asperlin.
First published: 24 June 2010
Abstract
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ChemInform Abstract
Biologically active title compounds (VIII) and (IX) are synthesized starting with Ferrier′s diol (I). The configuration at C-5 of bicyclic key intermediate (III) corresponds to that of the hexapyranosides in the L-sugar series. Mitsunobu inversion of compound (VI) with AcOH leads to (+)-acetylphomalactone (VIII).
