1262023-33-5Relevant articles and documents
A short synthesis of (+) and (-)-falcarinol
McLaughlin, Noel P.,Butler, Eibhlín,Evans, Paul,Brunton, Nigel P.,Koidis, Anastasios,Rai, Dilip K.
experimental part, p. 9681 - 9687 (2011/02/25)
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.
