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

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논문

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

학술지

Green chemistry : an international journal and green chemistry resource : GC

저자명

Badland, Matthew; Burns, Michael P.; Carroll, Robert J.; Howard, Roger M.; Laity, Daniel; Wymer, Nathan J.

초록

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 salmonicolor aldehyde reductase in this bioreduction is also presented. Graphic AbstractApplication of multiple biocatalytic steps to access a potent β-3 receptor agonist. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c1gc15694b'>

발행연도

2011

발행기관

Royal Society of Chemistry

ISSN

1463-9262

ISSN

1463-9270

권

호

페이지

pp.2888-2894