Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity.
Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]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.
Thuring
Jan Willem J. F.
JW
NSR-Center for Molecular Structure, Design and Synthesis, Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525 ED Nijmegen, The Netherlands.
Nefkens
Gerard H. L.
GH
Wegman
Margreth A.
MA
Klunder
Antonius J. H.
AJ
Zwanenburg
Binne
B