Synthesis of Nonano-9-lactone Fused to a δ-Lactone Ring


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With the goal of obtaining fused dilactones, the carbohydrate moiety of diastereoisomeric Michael adducts of levoglucosenone and cyclohexanone was converted to δ-lactone and its derivatives fused to an octahydrochromene fragment. The subsequent oxidative cleavage of the C-C bridge in the latter by the action of pyridiniun chlorochromate (PCC) afforded nonano-9-lactone fused at the C6-C7 bond to δ-lactone or methyl-δ-lactol. The presence of a carbonyl group in the carbohydrate moiety was found to prevent C-C bond cleavage.

作者简介

L. Faizullina

Ufa Institute of Chemistry, Ufa Federal Research Center

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Email: sinvmet@anrb.ru
俄罗斯联邦, Ufa, 450054

A. Tagirov

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: sinvmet@anrb.ru
俄罗斯联邦, Ufa, 450054

Sh. Salikhov

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: sinvmet@anrb.ru
俄罗斯联邦, Ufa, 450054

F. Valeev

Ufa Institute of Chemistry, Ufa Federal Research Center

Email: sinvmet@anrb.ru
俄罗斯联邦, Ufa, 450054

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