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Communication | Regular issue | Vol 3, No. 9, 1975, pp.697-701
Published online, 1st January, 1970
DOI: 10.3987/R-1975-09-0697
Nitrogen Inversion in Solasodine N-Methyl and N-Formyl Derivatives

Genjiro Kusano, Tsunematsu Takemoto,* Norio Aimi, Herman J. C. Yeh, and David F. Johnson

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

O-Acetyl-N-methylsolasodine A (III) and B (IV), O-Acetyl-N-formylsolasodine A (V) and B (VI) are prepared. III and IV are interconvertible under acidic condition or at high temperature. Procedure of recrystallization of the mixture of III and IV precipitates III alone. V are reduced to N-methylsolasodine B (XI), while VI are reduced to a mixture of N-methylsolasodine A (X) and B (XI). These isomers are described as a result of nitrogen inversion.