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

Upon gold catalysis, the 2,3-dihydropyrrolo[1,2- ]indole motif, encountered in few but interesting bioactive natural products, was efficiently obtained from -aryl 2-alkynylazetidine derivatives. In an attempt to apply this methodology to the synthesis of harmalidine, isolated from the seeds of , adv...

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Bibliographic Details
Published in:RSC advances 2022-09, Vol.12 (41), p.26966-26974
Main Authors: Miaskiewicz, Solène, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien
Format: Article
Language:English
Subjects:
Chemical Sciences
Chemistry
Gold
Natural products
NMR
Nuclear magnetic resonance
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Summary:Upon gold catalysis, the 2,3-dihydropyrrolo[1,2- ]indole motif, encountered in few but interesting bioactive natural products, was efficiently obtained from -aryl 2-alkynylazetidine derivatives. In an attempt to apply this methodology to the synthesis of harmalidine, isolated from the seeds of , advanced amino 2,3-hydropyrrolo[1,2- ]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 -methylharmaline show discrepancies with the proposed natural product structure.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra05685b