Various (R)-and (S)-l-trimethylsilyl-l-alkyn-3-ols, chiral building units useful for the synthesis of biologically active compounds, have been efficiently resolved by enantioselective acetylation mediated by immobilized lipase PS. The resolution is applied to the synthesis of (R)-and (S)-5-octyl-2-(
Strategies for the chemoenzymatic preparation of optically active 1-alkyn-3-ols
✍ Scribed by B.I. Glänzer; K. Königsberger; B. Berger; K. Faber; H. Griengl
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 428 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
A series of (R)-and (S)-l-alkyn-3-ols, chiral building units for the synthesis of leukotrienes and pheromones, were prepared via enantioselective hydrolysis of their racemic esters. While the majority of biocatalysts employed (lipases, fermenting or freezedried microorganisms) failed in discriminating between enantiomers, lyophilized cells of baker's yeast (Saccharomyces cerevisiae Hansen) gave (S)-l-alkyn-3-ols and their corresponding (R)-esters with > 90% e.e.
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