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Synlett 1997; 1997(5): 600-602
DOI: 10.1055/s-1997-3223
DOI: 10.1055/s-1997-3223
letter
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The Thia-Analog of Ambrettolide. Synthesis and Odor of 1,8-Oxathiacyclohexadecan-2-one
Further Information
Publication History
Publication Date:
31 December 2000 (online)
The thia-analog of ambrettolide, 1,8-oxathiacyclohexadecan-2-one (3), was synthesized from ℇ-caprolactone (4). Cleavage of 4 with trimethylsilyl iodide in the presence of ethanol provided iodoester 5, that was converted to the thioether 6 by treatment with tetramethylthiourea and the monoalkoxide of 1,8-octanediol. Collaud cyclization furnished the target compound 3 that contrary to thiocyclopentadecanolides 7, 8 and 9 possesses an intense musk odor.
cyclization - macrolides - odorants - thia-analogs - thioether