jo9610220_si_001.pdf (160.58 kB)
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
journal contributionposted 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[5.2.1.02,6]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.