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RESEARCH PRODUCT
Stereoselective Synthesis of the Glycosidase Inhibitor Australine through a One-Pot, Double-Cyclization Strategy
J. Alberto MarcoCelia RibesE. FalomirMiguel Cardasubject
chemistry.chemical_classificationAldehydesKetoneGlycoside HydrolasesMolecular StructureBicyclic moleculeStereochemistryOrganic ChemistryConvergent synthesisStereoisomerismKetonesBiochemistryAldehydechemistry.chemical_compoundBenzylaminechemistryAldol reactionCyclizationPyrrolizidineSN2 reactionEnzyme InhibitorsPhysical and Theoretical ChemistryPyrrolizidine Alkaloidsdescription
[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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-12-06 | Organic Letters |