Facile Synthesis of β-Hydroxy-γ-Varelolactone via the Ring Opening Reaction of β-Trichloromethyl-β-Propiolactone with Ester Enolates
Access this Article
Search this Article
The reaction of enantiomerically pure (<I>S</I>)-β-trichloromethyl-β-propiolactone with enolate derived from <I>t</I>-butyl acetate gave δ-hydroxy-β-ketoester in good yield. Subsequent <I>syn</I>-selective reduction of ketone and cyclization gave β-hydroxy-γ-varelolactones in good yield in enantiomerically pure form. The β-hydroxy-γ-varelolactones thus obtained are excellent precursors for the synthesis of compactin and mevinolin derivatives of potent inhibitor of hydroxymethylglutaryl coenzyme A reductase (HMG CoA reductase).
- Chemistry Letters
Chemistry Letters 1997(8), 765-766, 1997-08
The Chemical Society of Japan