Organic letters

Stereocontrolled Synthesis of Kelsoene by the Homo-Favorskii Rearrangement

L Zhang, M Koreeda

文献索引：Zhang, Liming; Koreeda, Masato Organic Letters, 2002 , vol. 4, # 21 p. 3755 - 3758

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被引用次数: 21

摘要

(±)-Kelsoene (4) has been synthesized from 2, 5-dihydroanisole in 16 steps in 12.5% overall yield. The key step involves a base-catalyzed reaction of γ-keto tosylate (5), which effects a homo-Favorskii rearrangement to 16 as well as the corresponding intramolecular SN2 product 15 from the enolate of 5. Ketone 15 can efficiently be isomerized to cyclobutanone 17 having the kelsoene carbon skeleton upon acid treatment.