Stereoselective synthesis of the glycosidase inhibitor australine through a one-pot, double-cyclization strategy
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Updated: Jul 18, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Celia Ribes1, Eva Falomir, Miguel Carda
1Departament de Química InorgAnica y OrgAnica, Universitat Jaume I, Castellón, E-12080 Castellón, Spain.
Abstract:
[reaction: see text] A stereocontrolled, convergent synthesis of the alkaloid australine, a glycosidase inhibitor of the pyrrolizidine class, is described. The chiral starting materials were ketone 3, derived from L-erythrulose, and alpha-alkoxy aldehyde 4, prepared from L-malic acid. A key step of the synthesis was the highly stereoselective aldol reaction between 4 and a Z boron enolate derived from 3. Another key step was the one-pot construction of the bicyclic pyrrolizidine system by means of a three-step sequence of SN2 displacements induced by benzylamine on a trimesylate precursor.
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