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

doi:10.1039/c2ob06904k

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

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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 language	English
Pages (from-to)	2774-2779
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	14
Early online date	18 Jan 2012
DOIs	https://doi.org/10.1039/c2ob06904k
Publication status	Published - 2012

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry
Medicine(all)

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10.1039/c2ob06904k

Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine†
© The Royal Society of Chemistry 2012 This is an open access Creative Commons Attribution-NonCommercial License (https://creativecommons.org/licenses/by-nc/3.0/), which permits use, distribution and reproduction for non-commercial purposes, provided the author and source are cited.
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Cite this

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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.",

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AU - Boyd, Derek R.

AU - D. Sharma, Narain

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AU - McIntyre, Peter B. A.

AU - Stevenson, Paul J.

AU - Allen, Christopher C. R.

PY - 2012

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AB - 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.

U2 - 10.1039/c2ob06904k

DO - 10.1039/c2ob06904k

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 14

ER -

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

Abstract

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