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Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis

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Abstract

Two novel pyrrolo[2,3-b]indole alkaloids, named robustanoids A (1) and B (2), featuring an unprecedented 1,2,3,4,8b,8c-hexahydro-2a,4a-diazapentaleno[1,6-ab]indene moiety, were isolated from Coffea canephora beans. Their structures were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. The total synthesis of compounds 1 and 2 was successfully conducted to give a decent total yield (∼29%) in 8 steps, which also confirmed the structures determined by spectroscopic data. Compound 2 showed α-glucosidase inhibitory activity comparable to that of the positive control, acarbose.

Graphical abstract: Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis

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Publication details

The article was received on 12 Oct 2017, accepted on 31 Oct 2017 and first published on 01 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00931C
Citation: Org. Chem. Front., 2018, Advance Article
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    Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis

    J. Han, S. Niu, Y. Liu, L. Gan, T. Wang, C. Lu and T. Yuan, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00931C

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