ChemInform Abstract: Asymmetric Synthesis of Goniothalamin, Hexadecanolide, Massoia Lactone, and Parasorbic Acid via Sequential Allylboration-Esterification Ring-Closing Metathesis Reactions.

Abstract

Abstract Acrylic esters of homoallylic alcohols prepared in 92–97% ee via the asymmetric allylboration of appropriate aldehydes with B -allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of ( S )-(+)-parasorbic acid, ( R )-(–)-massoia lactone, and ( R )-(+)-goniothalamin. ( S )-(–)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence.