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

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

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)


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
Issue number51
Publication statusPublished - 18 Dec 2011

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery


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