title: 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.
abstract: 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.
authors.affiliation: NSR-Center for Molecular Structure, Design and Synthesis, Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525 ED Nijmegen, The Netherlands.
authors.forename: Jan Willem J. F.
authors.initials: JW
authors.lastname: Thuring
authors.forename: Gerard H. L.
authors.initials: GH
authors.lastname: Nefkens
authors.forename: Margreth A.
authors.initials: MA
authors.lastname: Wegman
authors.forename: Antonius J. H.
authors.initials: AJ
authors.lastname: Klunder
authors.forename: Binne
authors.initials: B
authors.lastname: Zwanenburg