Chemoenzymatic formal synthesis of (?)- and (+)-epibatidine?

Organic & Biomolecular Chemistry Pub Date: 2012-01-18 DOI: 10.1039/C2OB06904K

Abstract

The cis-dihydrocatechol, derived from enzymatic cis-dihydroxylation of bromobenzene using the microorganism Pseudomonas putida UV4, was converted into (?)-epibatidine in eleven steps with complete stereocontrol. In addition, an unprecedented palladium-catalysed disproportionation reaction gave the (+)-enantiomer of an advanced key intermediate employed in a previous synthesis of epibatidine.

Graphical abstract: Chemoenzymatic formal synthesis of (?)- and (+)-epibatidine
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