Enantioselective synthesis of a fluorinated analogue of the orsellinic acid-type twelve-membered lactone lasiodiplodin.
The chemoenzymatic synthesis of the racemate and the one enantiomer of the fluorinated analogue 8 of the natural cyclooxygenase inhibitor lasiodiplodin is decribed. A lipase-mediated deracemization of the fluorohydrin 18 provided the chiral, nonracemic building block for the enantioselective synthesis of the title compound. The key step was the formation of the 12-membered lactone by a ring-closing metathesis.
Runge
M
M
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstr. 40, D-48149 Münster, Germany.
Haufe
G
G
D005461:Fluorine / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013237:Stereoisomerism; D015025:Zearalenone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*
C418130:7-fluoromethyl-2,4-dimethoxy-7,8,9,10,11,12,13,14-octahydro-6-oxabenzocyclododecan-5-one; D007783:Lactones; C417552:lasiodiplodin; D005461:Fluorine; D015025:Zearalenone