A synthetic approach to the quassinoids

CH Heathcock, C Mahaim, MF Schlecht…

文献索引：Heathcock, Clayton H.; Mahaim, Cyril; Schlecht, Matthew F.; Utawanit, Thanin Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3264 - 3274

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被引用次数: 58

摘要

A synthetic route to the quassinoids has been developed. Two-stage annelation of 2- methylcyclohexanone with 1-chloro-3-pentanone gives tricyclic dienone 9 (60%), which is oxidized by acetyl chromate in acetic acid to give dienedione 27 (80%). Bisketalization of this material followed by hydrolysis of the conjugated enone ketals provides monoketal30 (77%), along with recovered 27. Ring C of 30 is functionalized by the Stiles and Reich ...