A general approach to the stereoselective synthesis of spiroketals. A total synthesis of the pheromones of the olive fruit fly and related compounds

P DeShong, RE Waltermire…

文献索引：Deshong,P.; Waltermire,R.E.; Ammon,H.L. Journal of the American Chemical Society, 1988 , vol. 110, p. 1901

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被引用次数: 66

摘要

Abstract: A general, highly stereoselective approach to the synthesis of spiroketal systems of the 1, 7-dioxaspiro [5.51 undecane and l, ddioxaspiro [4S] decane families is discussed. The key reaction in the approach features oxidation of a suitably substituted furfurol derivative 1 to afford pyranone 2, which subsequently undergoes stereoselective intramolecular ketalization under acidic conditions to furnish spiroketal 3, carrying the 2, 6-anti ...