Yongxin Zhang, Shucheng Wang, Yaodong Huang
Nov 23, 2020
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Journal
Frontiers of Chemical Science and Engineering
Abstract
A convenient and highly efficient method is described for the synthesis of N -methoxycarbazole derivatives, including those with sterically demanding, benzannulated, or strongly electron-donating or -withdrawing substituents. Various N -methoxycarbazole derivatives were directly prepared in good-to-moderate yields by the Pd 2 (dba) 3 CHCl 3 /9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene-catalyzed reactions of the corresponding dibromobiphenyl compounds and methoxyamine. Based on this methodology, the first total synthesis of 3,3′-[oxybis(methylene)]bis(9-methoxy-9 H -carbazole), an antimicrobial dimeric carbazole alkaloid previously isolated from the stem bark of Murraya koenigii , was achieved in 18% yield over seven steps from 1,2-dibromobenzene.