An unusual oxidation of an NCH3 group to an NCHO group by osmium tetroxide |
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| Authors: | S.William Pelletier Haridutt K. Desai Janet Finer-Moore Naresh V. Mody |
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| Affiliation: | Institute for Natural Products Research and The Department of Chemistry The University of Georgia, Athens, Georgia 30602, U.S.A. |
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| Abstract: | Treatment of pyrodelphinine (1) with osmium tetroxide afforded a mixture of the cis-hydroxylation product 2 and an unexpected product 3 in the ratio of 4:1, respectively. Similarly, oxidation of delphinine (5) afforded α-oxodelphinine (6; 75%) and oxidation of mesaconitine (8) furnished oxonitine (9; 92%). Thus a very selective oxidation of the N-methyl group of delphinine and mesaconitine is effected osmium tetroxide. |
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