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Synlett 1998; 1998(1): 31-32
DOI: 10.1055/s-1998-1574
DOI: 10.1055/s-1998-1574
letter
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A Mild, Efficient and General Method for the Synthesis of Trialkylsilyl (Z)-4-Oxo-2-alkenoates and γ-Hydroxybutenolides
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Publication History
Publication Date:
31 December 2000 (online)
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.
γ-hydroxybutenolides - trialkylsilyl (Z)-4-oxo-2-alkenoates - 2-trialkylsilyloxyfurans - dimethyldioxirane - oxidation