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Umsetzung von 3‐O‐Acetyl‐14‐anhydrodigitoxigenin und 3‐O‐Acetyldigitoxigenin mit Osmiumtetroxid
Author(s) -
Schüpbach M.,
Krasso A. F.,
Binder M.,
Tamm Ch.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540730
Subject(s) - chemistry , butenolide , digitoxigenin , acetylation , stereochemistry , diol , ring (chemistry) , organic chemistry , glycoside , biochemistry , gene
Treatment of 3‐O‐acetyl‐14‐anhydrodigitoxigenin ( 1 ) with 1.1 equivalents of OsO 4 gave both the 14α, 15α‐diol 2 and the 14β, 15β‐diol 4. Degradation to the corresponding methyl etianates 7 and 10 , respectively, established their stereochemistry. Treatment of both the 14‐hydroxy‐15‐acetoxy‐cardenolides 3 and 5 with OsO 4 leads to the expected mixtures of 20, 22‐diols, a partial separation of which was achieved after acetylation. The butenolide ring of 3‐O‐acetyl‐digitoxigenin ( 25 ) also reacted with OsO 4 , yielding the two 20,22diols 26 and 27 , the stereochemistry of which has tentatively been assigned on the basis of NMR. data.