1. An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides.
- Author
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Ruan, Libo, Shi, Min, Mao, Shiwei, Yu, Lifang, Yang, Fan, and Tang, Jie
- Subjects
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BENZOFURANS , *CHALCONES , *EPOXY compounds , *REARRANGEMENTS (Chemistry) , *DEHYDRATION reactions , *RING formation (Chemistry) , *BENZOIN - Abstract
Abstract: An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3·Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2-methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%–100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently. [Copyright &y& Elsevier]
- Published
- 2014
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