Chemistry of Natural Compounds p. 67 - 71 (1985)
Update date:2022-08-05
Topics:
Makarevich, I. F.
Dikan', L. N.
The products of the autooxidation of the cardenolides strophanthidin and erysimin in solutions have been studied.It has been established that the autooxidation of 19-oxocardenolides forms, together with 19-carboxylic acids, a complex mixture of 19-norcardenolides.The bulk of them consists of 10β-OH compounds and a smaller proportion of 10β-H compounds.Autooxidation affects both the functional group at C-10 and its transformation and also other groupings and bonds in ring A and, to some extent, in ring B, including the oxidation of the 3β-OH group, degradation of the 5β-OH group, and cleavage of the C5-C10 bond with the formation of 5,10-seco-19-norcardenolides.A possible mechanism of the formation of 19-norcardenolides is discussed.
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Doi:10.1021/ja01866a043
(1940)Doi:10.1039/jr9610003633
(1961)Doi:10.1039/c7tc05775j
(2018)Doi:10.1021/ja00309a029
(1985)Doi:10.1039/b718209k
(2008)Doi:10.1016/S0040-4039(01)80829-7
(1985)