A highly efficient methodology for the preparation of

2021, Volume 15, Issue 3

Abstract

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Frontiers of Chemical Science and Engineering >> 2021, Volume 15, Issue 3 doi: 10.1007/s11705-020-1979-9

A highly efficient methodology for the preparation of

Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China

Received: 2020-09-24 Accepted: 2020-11-23 Available online: 2020-11-23

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Abstract

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

Keywords

N-methoxyl carbazole ; dimeric N-methoxyl carbazole ; alkaloid ; total synthesis ; double N-arylation of methoxyamine

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