Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: useful intermediates for the synthesis of optically active γ-lactones

✍ Scribed by Pietro Allevi; Pierangela Ciuffreda; Mario Anastasia

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 426 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(96)00475-2

✦ Synopsis

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-(5H)-furanones. (~) 1997, Elsevier Science Ltd. All rights reserved.

Optically active 1-trimethylsilyl-l-alkyn-3-ols 1 or 1-alkyn-3-ols 2 are of synthetic value as precursors of many biologically active natural products. 1 In fact, by carboxylation of alkynols 2 (Z)-4-hydroxy-2-alkenyl acids are obtained, which are key intermediates in the total synthesis of such naturally occurring compounds as unsaturated or saturated lactones and bislactones, 2 leucotrienes, prostaglandins, vitamin E and steroids. 3