ChemInform Abstract: A Novel Entry to Naturally Occurring 5‐Alkenyl α,β‐Unsaturated δ‐Lactones from D‐Glucose: Syntheses of (+)‐Acetylphomalactone and (+)‐Asperlin.

Abstract

A Novel Entry to Naturally Occurring 5-Alkenyl α,β-Unsaturated δ-Lactones from D-Glucose: Syntheses of (+)-Acetylphomalactone and (+)-Asperlin.-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). -(GOMEZ, A. M.; LOPEZ DE URALDE, B.; VALVERDE, S.; LOPEZ, J. C.; Chem.