Authors
Alessandro Brusa, Matteo Bottiglieri, Carola Tomassi, Francesco Feola, Daniele Lanaro, Andrea Bonetti, Gabriella Zappia, Federico Sala, Andrea Gambini, Mario Falzoni, Pietro Allegrini, Maria Luisa Gelmi, Massimiliano Aschi, Andrea Mazzanti, Fabio Pesciaioli, Armando Carlone
Published in
Organic process research & development. Volume 30. Issue 7. Pages 1789-1796. Jul 17, 2026. Epub Jun 25, 2026.
Abstract
A process-friendly and enantioselective total synthesis of (S)-autumnaline, a key biosynthetic precursor to the colchicine alkaloids, is reported. The strategy relies on a Bischler-Napieralski cyclization-asymmetric imine reduction sequence to construct the chiral isoquinoline core. Significant process innovations include a cyanide-free homologation using a Darzens reaction and a chromatography-free purification strategy via d-tartrate salt formation. The absolute configuration was definitively confirmed through a combination of circular dichroism (CD) spectroscopy and computational modeling. This developed process affords (S)-autumnaline in 11 steps (nine-step longest linear sequence) with a 13% overall yield.
PMID:
42553890
Bibliographic data and abstract were imported from PubMed on 05 Aug 2026.
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