American Chemical Society
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Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity

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journal contribution
posted on 1996-10-04, 00:00 authored by Jan Willem J. F. Thuring, Gerard H. L. Nefkens, Margreth A. Wegman, Antonius J. H. Klunder, Binne Zwanenburg
Racemic 5-hydroxy-4-oxa-endo-tricyclo[,6]dec-8-en-3-one and its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.