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.
Original language | English |
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Pages (from-to) | 9681-9687 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 66(51) |
Issue number | 51 |
DOIs | |
Publication status | Published - 18 Dec 2011 |
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery