Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration–esterification ring-closing metathesis reactions

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.