A short synthesis of (+) and (−)-falcarinol |
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Authors: | Noel P. McLaughlin Paul Evans Nigel P. Brunton Anastasios Koidis Dilip K. Rai |
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Affiliation: | a Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Irelandb Teagasc Food Research Centre Ashtown, Ashtown, Dublin 15, Ireland |
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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. |
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Keywords: | Phytochemical Polyacetylene natural product Acetylide alkylation Enzymatic kinetic resolution |
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