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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 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 ZwanenburgRacemic
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.