Chemoenzymatic formal synthesis of ()- and (+)-epibatidineElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR spectra. See DOI: 10.1039/c2ob06904k

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...

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Main Authors: Boyd, Derek R, Sharma, Narain D, Kaik, Magdalena, M Intyre c, Peter B. A, Stevenson, Paul J, Allen, Christopher C. R
Format: Article
Language:English
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Summary: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. The (+)-1,2-dihydrodiol metabolite from bromobenzene was converted in four steps to an aminoalcohol intermediate and then a further seven steps into () or (+)-epibatidine.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob06904k