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

被引：8

作者：

Badland, Matthew ^{[1
]}

Burns, Michael P. ^{[2
]}

Carroll, Robert J. ^{[1
]}

Howard, Roger M. ^{[1
]}

Laity, Daniel ^{[1
]}

Wymer, Nathan J. ^{[2
]}

机构：

[1] Pfizer Worldwide Res & Dev, Sandwich Labs, Sandwich CT13 9NJ, Kent, England

[2] Pfizer Worldwide Res & Dev, Chem Res & Dev, Groton, CT 06340 USA

来源：

GREEN CHEMISTRY | 2011年 / 13卷 / 10期

关键词：

CARBONYL REDUCTASE; DISCOVERY; KETONES; POTENT;

D O I：

10.1039/c1gc15694b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemoenzymatic syntheses of two key intermediates in the preparation of a potent beta-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.

引用

页码：2888 / 2894

页数：7

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