| Autor: |
Glueck, Silvia M., Fabian, Walter M. F., Faber, Kurt, Mayer, Sandra F. |
| Zdroj: |
Chemistry - A European Journal; July 2004, Vol. 10 Issue: 14 p3467-3478, 12p |
| Abstrakt: |
Asymmetric enzyme‐catalyzed hydrolysis of methylene‐interrupted bis‐epoxides 1 aand 1 bcatalyzed by bacterial epoxide hydrolases furnished tetrahydrofuran derivatives 2 aand 2 bthrough a hydrolysis–rearrangement cascade. Whereas racemic bis‐oxiranes 1 b–dunderwent kinetic resolution with moderate stereoselectivities to yield products with up to 92 % eeand 66 % de: meso‐bis‐oxirane cis,cis‐1 awas transformed into (6R,7R,9S,10S)‐2 ain 94 % eeand 89 % deat high conversion (85 %) by Rhodococcussp. 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. |
| Databáze: |
Supplemental Index |
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