Substitution of the angular aldehyde by halogen in cardiosteroids in two steps was studied. The first step was oxidation of the aldehyde and production of the cooresponding 19-carboxylic acids; the second, decarboxylation of the 19-carboxylic acids using N-chlorosuccinimide or chloride salts. The 10-chloro-19norcardiosteroids: 10-chloro-19-norstrophanthidine (1), 10-chloro-19-norcymarin (2), 10-chloro-19norconvallatoxin (3), 10-chloro-19-norstrophalloside (4), and 10-chloro-19-norbovoside A (5) were prepared for the first time. The intermediates strophalloside-19-carboxylic acid and bovoside A-19-carboxylic acid were also prepared for the first time and characterized.
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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 549–551, September–October, 2009.
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Makarevich, I.F., Ulesov, A.V. & Nestertsova, I.A. 10-chloro-19-norcardiosteroids. Chem Nat Compd 45, 653–655 (2009). https://doi.org/10.1007/s10600-009-9440-9
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DOI: https://doi.org/10.1007/s10600-009-9440-9