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Issue 10, 2011
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Application of biocatalysis towards asymmetric reduction and hydrolytic desymmetrisation in the synthesis of a β-3 receptor agonist

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Abstract

Chemoenzymatic syntheses of two key intermediates in the preparation of a potent β-3 receptor agonist 1 are described. A lipase-catalysed hydrolytic desymmetrisation is employed in a new synthesis of intermediate 7, which avoids the use of alkyl-tin reagents. A second biotransformation delivers chiral chlorohydrin 5 from its parent ketone in greater enantiomeric excess than the previously-described Noyori-reduction process. A brief discussion of the enantioselectivity of a set of single-point mutants of Sporobolomyces salmonicoloraldehyde reductase in this bioreduction is also presented.

Graphical abstract: Application of biocatalysis towards asymmetric reduction and hydrolytic desymmetrisation in the synthesis of a β-3 receptor agonist

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Article information


Submitted
14 Jun 2011
Accepted
04 Aug 2011
First published
01 Sep 2011

Green Chem., 2011,13, 2888-2894
Article type
Paper

Application of biocatalysis towards asymmetric reduction and hydrolytic desymmetrisation in the synthesis of a β-3 receptor agonist

M. Badland, M. P. Burns, R. J. Carroll, R. M. Howard, D. Laity and N. J. Wymer, Green Chem., 2011, 13, 2888
DOI: 10.1039/C1GC15694B

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