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Total synthesis of dl-quadrone

S Danishefsky, K Vaughan, R Gadwood…

文献索引:Danishefsky, Samuel; Vaughan, Kenward; Gadwood, Robert; Tsuzuki, Kazuo Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4136 - 4141

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被引用次数: 104

摘要

Abstract: A regio-and stereospecific total synthesis of dl-quadrone (1) is described. The synthesis, which starts with 4, 4-dimethylcyclopent-2-en-l-one (9, is accomplished in 19 steps in 3.1% yield. The key intermediates are the enone ester 4, the iodo ketal 15, the tricyclic keto ester 16, and the hydroxymethyl keto acid 22. The latter as well as the seco acid 2 afford quadrone upon thermolysis.