Synthese Aldosteron‐ähnlicher Corticosteroide. d,l‐18‐Hydroxycorticosteron und d, l‐18‐Desoxyaldosteron

Abstract

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.