An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

作者：Ruan Libo; Shi Min; Mao Shiwei; Yu Lifang; Yang Fan^*; Tang Jie

来源：Tetrahedron, 2014, 70(5): 1065-1070.

DOI：10.1016/j.tet2013.12.050

• 2-Arylbenzo[b]furans
• 2-Methoxychalcone epoxides
• Deformylation
• Cyclodehydration
• Stemofuran A

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 2methoxydeoxybenzoins. 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.

• 出版日期2014-2-4
• 单位华东师范大学