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Visible light photoredox catalyzed semisynthesis of the analogues of maclekarpine E: a series of 6-vinyl substituted dihydrobenzophenanthridine alkaloids

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Abstract

A visible light promoted vinylation of N-methyl 5,6-dihydrobenzophenanthridine was developed to synthesize the analogues of maclekarpine E. In this photoredox neutral radical coupling reaction, an α-amino C-radical generated at the C-6 of N-methyl 5,6-dihydrobenzophenanthridine was the key intermediate. The subsequent radical addition of vinyl sulfones with the α-amino C-radical followed by elimination of a sulfinyl radical gave the target compounds in moderate to good yields.

Graphical abstract: Visible light photoredox catalyzed semisynthesis of the analogues of maclekarpine E: a series of 6-vinyl substituted dihydrobenzophenanthridine alkaloids

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Publication details

The article was received on 22 Jul 2017, accepted on 03 Oct 2017 and first published on 11 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00617A
Citation: Org. Chem. Front., 2018, Advance Article
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    Visible light photoredox catalyzed semisynthesis of the analogues of maclekarpine E: a series of 6-vinyl substituted dihydrobenzophenanthridine alkaloids

    Z. Qing, H. Cao, P. Cheng, W. Wang, J. Zeng and H. Xie, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00617A

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