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

作者：McLaughlin Noel P; Butler Eibhlin; Evans Paul^*; Brunton Nigel P; Koidis Anastasios; Rai Dilip K

来源：Tetrahedron, 2010, 66(51): 9681-9687.

DOI：10.1016/j.tet.2010.10.049

• Phytochemical
• Polyacetylene natural product
• Acetylide alkylation
• Enzymatic kinetic resolution

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.

• 出版日期2010-12-18