A Mild, Efficient and General Method for the Synthesis of Trialkylsilyl (Z)-4-Oxo-2-alkenoates and γ-Hydroxybutenolides

1 January 1998

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1998 (01) , 31-32
https://doi.org/10.1055/s-1998-1574

Abstract

2-Trialkylsilyloxyfurans react rapidly with dimethyldioxirane at -78 °C to provide trialkylsilyl (Z)-4-oxo-2-alkenoates whose hydrolysis delivers γ-hydroxybutenolides with high efficiency; a short synthesis of a naturally occurring monoterpene γ-hydroxybutenolide (4) is reported.

Keywords

Γ-HYDROXYBUTENOLIDES
TRIALKYLSILYL (Z)-4-OXO-2-ALKENOATES
2-TRIALKYLSILYLOXYFURANS
DIMETHYLDIOXIRANE
OXIDATION

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