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ChemInform Abstract: Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo(5.2.1.02, 6)dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity.

✍ Scribed by J. W. J. F. THURING; G. H. L. NEFKENS; M. A. WEGMAN; A. J. H. KLUNDER; B. ZWANENBURG


Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Enzymatic

Kinetic Resolution of 5-Hydroxy-4-oxa-endotricyclo(5.2.1.02, 6)dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity.

-Racemic tricyclic hydroxy lactones (I) and (V) are resolved employing a lipase-catalyzed acetylation reaction. The kinetic resolution is accompanied by a remarkable epimerization at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of furanone (VIII). -(THURING,