Biocatalytic asymmetric rearrangement of a methylene-interrupted bis-epoxide: simultaneous control of four asymmetric centers through a biomimetic reaction cascade

Chemistry : a European Journal
Silvia M GlueckSandra F Mayer

Abstract

Asymmetric enzyme-catalyzed hydrolysis of methylene-interrupted bis-epoxides 1 a and 1 b catalyzed by bacterial epoxide hydrolases furnished tetrahydrofuran derivatives 2 a and 2 b through a hydrolysis-rearrangement cascade. Whereas racemic bis-oxiranes 1 b-d underwent kinetic resolution with moderate stereoselectivities to yield products with up to 92 % ee and 66 % de: meso-bis-oxirane cis,cis-1 a was transformed into (6R,7R,9S,10S)-2 a in 94 % ee and 89 % de at high conversion (85 %) by Rhodococcus sp. CBS 717.73 as the major product. The reaction sequence resembles a biomimetic reaction cascade and provides an efficient entry into the structural core of annonaceous acetogenins with simultaneous control of four stereocenters.

Citations

Nov 4, 2008·Chemistry : a European Journal·Michael EggerBurkhard König
Jul 3, 2009·Angewandte Chemie·Ivan Vilotijevic, Timothy F Jamison
Sep 29, 2019·International Journal of Molecular Sciences·Hanna BuschUlf Hanefeld
Jul 24, 2020·Chemistry, an Asian Journal·Rodney A FernandesDnyaneshwar A Gorve
Feb 13, 2007·Bioorganic & Medicinal Chemistry Letters·J R FalckXiu-Yu Yi
Apr 30, 2011·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
May 10, 2017·Chemical Reviews·Joerg H SchrittwieserWolfgang Kroutil
Jul 13, 2011·The Journal of Organic Chemistry·Ross M DentonAndrew M Poulton

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