A short synthesis of (+) and (−)-falcarinol

Noel McLaughlin, E. Butler, Paul Evans, Nigel Brunton, Tassos Koidis, Dilip Rai

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess–Martin periodinane gave falcarinone 2.
Original languageEnglish
Pages (from-to)9681-9687
Number of pages7
JournalTetrahedron
Volume66(51)
Issue number51
DOIs
Publication statusPublished - 18 Dec 2011

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Fingerprint Dive into the research topics of 'A short synthesis of (+) and (−)-falcarinol'. Together they form a unique fingerprint.

  • Cite this

    McLaughlin, N., Butler, E., Evans, P., Brunton, N., Koidis, T., & Rai, D. (2011). A short synthesis of (+) and (−)-falcarinol. Tetrahedron, 66(51)(51), 9681-9687. https://doi.org/10.1016/j.tet.2010.10.049