The Journal of organic chemistry

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

E Fillion, AM Dumas, SA Hogg

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

Full Text: HTML

Citation Number: 29

Abstract

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.

Related Articles:

Organic reactions in ionic liquids: ionic liquid ethylammonium nitrate–promoted knoevenagel condensation of Meldrum's acid with aromatic aldehydes

[Hu, Yi; Wei, Ping; Huang, He; Le, Zhang-Gao; Chen, Zhen-Chu Synthetic Communications, 2005 , vol. 35, # 23 p. 2955 - 2960]

Synthesis of 5-arylidene-2, 2-dimethyl-1, 3-dioxane-4, 6-diones and coumarin-3-carboxylic acids via reaction of nitrones and Meldrum's acid

[Kumar, Dhruva; Suresh; Sandhu, Jagir S. Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013 , vol. 52, # 8 p. 1157 - 1160]

Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses

[Wang, Qi-Fang; Hui, Li; Hou, Hong; Yan, Chao-Guo Journal of Combinatorial Chemistry, 2010 , vol. 12, # 2 p. 260 - 265]

Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses

[Wang, Qi-Fang; Hui, Li; Hou, Hong; Yan, Chao-Guo Journal of Combinatorial Chemistry, 2010 , vol. 12, # 2 p. 260 - 265]

Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses

[Wang, Qi-Fang; Hui, Li; Hou, Hong; Yan, Chao-Guo Journal of Combinatorial Chemistry, 2010 , vol. 12, # 2 p. 260 - 265]

More Articles...