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

Derek R. Boyd, Narain D. Sharma, Magdalena Kaik, Peter B. A. McIntyre, Paul J. Stevenson, Christopher C. R. Allen

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)
179 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)2774-2779
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number14
Early online date18 Jan 2012
DOIs
Publication statusPublished - 2012

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Medicine(all)

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