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Selenium Dioxide Oxidation of Oxime derivative of Lupanone and Antimicrobial activity of the Oxidized Products

Author Affiliations

  • 1Department of Chemistry, University of North Bengal, P.O. North Bengal University, Dist. Darjeeling, 734 013, INDIA

Res.J.chem.sci., Volume 3, Issue (10), Pages 64-68, October,18 (2013)


Oxime derivative (1a) of lupanone (1) on oxidation with hydrogen peroxide and selenium dioxide in tertiary butanol furnishes a d-lactone, 4,23,24-tri-nor-lupan-3→5-olide (2) and 1-carboxy-2,3-seco-lupan-3→1—olide (3). The structures of these compounds have been fully established on the basis of spectral data (IR, MS, PMR, and 13-C NMR) and by comparison with reported data. Both the compounds showed better antimicrobial activity against all the microorganisms studied compared to the parent natural product, lupanone.


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