Stereoselective Synthesis of (2S,3S)-2-Benzyl-2-hydroxy-3- (3,4-methylenedioxybenzyl)-γ-butyrolactone from L-(+)-Arabinose via a Carissanol-type of Lignan

Abstract

  As a model experiment for the synthesis of optically active α,β-dibenzyl-α-hydroxy-γ-butyrolactone (1), (2S,3S)-2-benzyl-2-hydroxy-3-(3,4-methylenedioxybenzyl)-γ-buty-rolactone (3) was stereoselectively synthesized from L-(+)-arabinose via the carissanol-type of lignan, (2R/ S,3S,4S)-3-benzyl-2,3-dihydroxy-4-(3,4-methylenedio-xybenzyl)tetrahydrofuran (4).