The Journal of organic chemistry

Modular synthesis of tetrahydrofluorenones from 5-alkylidene Meldrum's acids

E Fillion, AM Dumas, SA Hogg

文献索引：Fillion, Eric; Dumas, Aaron M.; Hogg, Sylvia A. Journal of Organic Chemistry, 2006 , vol. 71, # 26 p. 9899 - 9902

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被引用次数: 29

摘要

The one-pot synthesis of tetrahydrofluorenones, the core 6-5-6 tricyclic structural motif found in norditerpenoid natural products, from alkylidene Meldrum's acids via thermal Diels- Alder/BF3⊙ OEt2-catalyzed Friedel-Crafts acylation reactions is described. A series of tetrahydrofluorenones was assembled in good yields, and the Diels-Alder/Friedel-Crafts acylation protocol allowed modification of the substitution within the rings.