Synthesis of Tetrahydronaphthalene Lignan Esters by Intramolecular Cyclization of Ethyl p-Azidophenyl-2-phenylalkanoates and Evaluation of the Growth Inhibition of …

…, F Piedade, MJ Calhorda, R Abramovitch…

Index: Pinto, Orlando; Sardinha, Joao; Vaz, Pedro D.; Piedade, Fatima; Calhorda, Maria J.; Abramovitch, Rudolph; Nazareth, Nair; Pinto, Madalena; Nascimento, Maria S. J.; Rauter, Amelia P. Journal of Medicinal Chemistry, 2011 , vol. 54, # 9 p. 3175 - 3187

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Citation Number: 5

Abstract

Intramolecular cyclization via nitrenium ion of 2-phenylpentanoic/2-phenylbutanoic acid esters with a terminal p-azidophenyl group gives direct access to tetrahydronaphthalene lignan esters. The p-azidophenyl-substituted butanoate led to an ethyl spirodienone carboxylate, while its homologue pentanoate gave ethyl 4-(4-aminophenyl)-1, 2, 3, 4- tetrahydronaphthalene-1-carboxylate in good yield. In contrast, the m-azidophenyl- ...