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Synthese Aldosteron‐ähnlicher Corticosteroide. d , l ‐18‐Hydroxycorticosteron und d , l ‐18‐Desoxyaldosteron
Author(s) -
Schmidlin J.,
Wettstein A.
Publication year - 1961
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.19610440619
Subject(s) - chemistry , yield (engineering) , hydrolysis , aldosterone , acetic acid , enantiomer , perchloric acid , stereochemistry , medicinal chemistry , organic chemistry , materials science , biology , metallurgy , genetics
d , l ‐18‐Hydroxy‐corticosterone (XII, XIII), the d‐enantiomer (I) of which is probably a direct biogenetic precursor of aldosterone (IIa, b), has been prepared. The synthesis leads from the trihydroxy‐diketal IV to the diacetate VI, in which the ketal groups could be split with a mixture of perchloric and acetic acid. The diacetoxydiketone IX thus obtained was hydrolysed under carefully controlled alkaline conditions to yield the 18‐monoacetate XI or the free d , l ‐18‐hydroxy‐corticosterone (XII). The latter compound exists, however, predominantly in the form of the (20→18)‐cyclohemiketal XIII, a conclusion reached from its infrared absorption spectrum and the comparatively slow reduction of tetrazolium salt.