Glueck_2004_Chemistry_10_3467

Reference

Title : Biocatalytic asymmetric rearrangement of a methylene-interrupted bis-epoxide: simultaneous control of four asymmetric centers through a biomimetic reaction cascade - Glueck_2004_Chemistry_10_3467
Author(s) : Glueck SM , Fabian WM , Faber K , Mayer SF
Ref : Chemistry , 10 :3467 , 2004
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.

PubMedSearch : Glueck_2004_Chemistry_10_3467
PubMedID: 15252793

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Citations formats

Glueck SM, Fabian WM, Faber K, Mayer SF (2004)
Biocatalytic asymmetric rearrangement of a methylene-interrupted bis-epoxide: simultaneous control of four asymmetric centers through a biomimetic reaction cascade
Chemistry 10 :3467

Glueck SM, Fabian WM, Faber K, Mayer SF (2004)
Chemistry 10 :3467