biostudies-literatureUnknown12(41)Miaskiewicz SUpon 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 discrepancRSC advances26966-26974https://www.ebi.ac.uk/biostudies/studies/S-EPMC9490519biostudies-literatureA gold(i)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala.PMC9490519Weibel JMPale PMiaskiewicz SBlanc AfalseA gold(i)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala.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 discrepanc2022-01-01T00:00:00Z2022 Sep2025-04-26T00:55:58.706Z2025-02-19T03:02:22.435ZS-EPMC94905193627516910.1039/d2ra05685b