Synthesis and resolution of a key building block for epothilones: a comparison of asymmetric synthesis, chemical and enzymatic resolution

G Scheid, E Ruijter, M Konarzycka-Bessler…

Index: Scheid, Guenther; Ruijter, Eelco; Konarzycka-Bessler, Monika; Bornscheuer, Uwe T.; Wessjohann, Ludger A. Tetrahedron Asymmetry, 2004 , vol. 15, # 18 p. 2861 - 2869

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Citation Number: 29

Abstract

The asymmetric synthesis and kinetic resolution of a series of acyloins (α-hydroxy ketones) suitable as building blocks for the northern half of epothilones was studied. Three methods were applied to obtain nonracemic compounds at the eventual epothilone C15-position: asymmetric synthesis with Evans' auxiliary, chemical resolution and enzymatic resolution. The success rate in small scale applications increased in the order given, and the ...