Issue 41, 2022

A gold(i)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala

Abstract

Upon gold catalysis, the 2,3-dihydropyrrolo[1,2-a]indole motif, encountered in few but interesting bioactive natural products, was efficiently obtained from N-aryl 2-alkynylazetidine derivatives. In an attempt to apply this methodology to the synthesis of harmalidine, isolated from the seeds of Peganum harmala, advanced amino 2,3-hydropyrrolo[1,2-a]indol(one) derivatives were readily obtained in only 11 steps from but-3-yn-1-ol. While the reported structure of harmalidine could not be reached from these intermediates, a surprising 12-membered diimino dimer was isolated. Extensive comparison of the reported harmalidine NMR data to the experimental and calculated data of our synthetic molecules, harmaline or the synthetised N-methylharmaline show discrepancies with the proposed natural product structure.

Graphical abstract: A gold(i)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala

Supplementary files

Article information

Article type
Paper
Submitted
09 set 2022
Accepted
13 set 2022
First published
21 set 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 26966-26974

A gold(I)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala

S. Miaskiewicz, J. Weibel, P. Pale and A. Blanc, RSC Adv., 2022, 12, 26966 DOI: 10.1039/D2RA05685B

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