DIANIONS OF β-HYDROXY SULFONES: NEW AND GENERAL APPROACH TO SELECTIVE SYNTHESIS OF 2(5<i>H</i>)-FURANONES

Abstract

Abstract Dianions derived from β-hydroxy sulfones are highly reactive toward a variety of electrophiles including alkyl halides, carbonyl compounds, and sodium iodoacetate. A convenient synthetic method for 4-alkyl- and 5-alkyl-2(5H)-furanones has been developed by using these dianions. A new synthetic approach to trans-3,4-bis(3-hydroxybenzyl)dihydro-2(3H)-furanone, the first lignan found in humans, via a facile reduction of 2(5H)-furanone with Mg-methanol is also decribed.