Uncommon Ozonolysis of 2,3-Seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile

The oxidation of 2,3-seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile with ozone in methylene chloride at –40°C afforded a mixture of 4,20-dioxo-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicar­bonitrile (71%), 4,20-dioxo-3,30-dihydroxy-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicarbonitrile (15%), 2,17-dicyano-2,4-seco-3,23,24,28,29,30-hexanorlupane-4,20-dioic acid (7%), and 30-hydroxy-2,4-seco-3,23,24,28,29-pentanorlupan-4-oic acid (4%). The product structure was determined by NMR spectroscopy using two-dimensional shift correlation techniques.