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

摘要

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)-(-)-Hexadecanoilide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence.