A short synthesis of (+) and (−)-falcarinol
NP McLaughlin, E Butler, P Evans, NP Brunton…
Index: McLaughlin, Noel P.; Butler, Eibhlin; Evans, Paul; Brunton, Nigel P.; Koidis, Anastasios; Rai, Dilip K. Tetrahedron, 2010 , vol. 66, # 51 p. 9681 - 9687
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Citation Number: 11
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- ...
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