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

P. Veeraraghavan Ramachandran, M. Venkat Ram Reddy, Herbert C. Brown

Research output: Contribution to journalArticle

112 Scopus citations

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. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)583-586
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number5
DOIs
StatePublished - Jan 29 2000

Keywords

  • Allylboration
  • Asymmetric synthesis
  • Metathesis

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