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Reaktionen mit Blei(IV)‐acetat, XVI . Eine neuartige Umwandlung von 2‐Acetoxy‐3‐oxo‐4,5‐epoxy‐steroiden
Author(s) -
Mihailović M. Lj.,
Foršek J.,
Lorenc Lj.,
Maksimovic Z.,
Fuhrer H.,
Kalvoda J.
Publication year - 1969
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.19690520213
Subject(s) - chemistry , stereochemistry , medicinal chemistry
Treatment of 3‐oxo‐4, 5‐oxido steroids with lead tetraacetate results in acetoxylation in the 2α‐position as could be shown by independent synthesis of the acetoxylated compounds. The products of this reaction rearrange even under very mild conditions (chromatography on silicagel or alumina) to the corresponding 2,3‐dioxo‐Δ 4 compounds. The influence of structure and conformation of the various intermediates on their NMR.‐spectra is discussed. A mechanism for this new transformation is proposed.