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

M Badland, MP Burns, RJ Carroll, RM Howard…

Index: Badland, Matthew; Burns, Michael P.; Carroll, Robert J.; Howard, Roger M.; Laity, Daniel; Wymer, Nathan J. Green Chemistry, 2011 , vol. 13, # 10 p. 2888 - 2894

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Citation Number: 8

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 ...