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Communication | Regular issue | Vol 16, No. 4, 1981, pp.581-590
Published online, 1st January, 1970
DOI: 10.3987/R-1981-04-0581
Oxidation of the 2,16 Double Bond of Vincadifformine

Georgette Hugel, Jean-Yves Laronze, Jacqueline Laronze, and Jean Lévy*

*Facluté de Pharmacie, UPRES-A/CNRS 6013, Insitut des Biomoleculés, 51, rue Cognacq-Jay, F-51096 Reims Cedex, France


Chemical vs photochemical oxidation of the 2,16 double bond of vincadifformine 1 and 3-oxo vincadifformine 2 yielded inter alia, respectively the ketoöxindoles 7 and 8. Attempts of partial synthesis of vincatine 15 from these derivatives were unsuccessful. The structure of the LAH reduction product of vincatine is revised to 21. The stereochemical course of an earlier total synthesis of vincadifformine is examined.