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Paper | Regular issue | Vol 27, No. 2, 1988, pp.393-399
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4373
Reaction of 2H-1-Benzopyrans with Organometallic Reagents. Synthesis of 4-(α,γ-Dialkyl-β-4-methoxyphenylallyl)resorcins

Angel Alberola,* Celia Andrés, Alfonso González Ortega, Rafael Pedrosa, and Martina Vicente

*Deparamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain


The stereoselective synthesis of E- and Z-4-(α,γ-dialkyl-β-4- methoxyphenylallyl)resorcins was accomplished by reaction of 2-alkyl-7- hydroxy-4’-methoxyisoflavenes with organoaluminum and organomagnesium reagents. This way leads to better yields than the reduction of 2,4-dialkyl- 7-hydroxy-4’-methoxyisoflavenes. The influence of substituents at different positions on the reduction was studied on model 2H-1-benzopyrans.