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Über 11,18‐dioxygenierte Progesterone. Über Steroide, 161. Mitteilung
Author(s) -
Schmidlin J.,
Wettstein A.
Publication year - 1959
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.19590420736
Subject(s) - chemistry , acetylation , ether , hydrolysis , stereochemistry , group (periodic table) , medicinal chemistry , organic chemistry , biochemistry , gene
The synthesis of several 11,18‐dioxygenated relatives (VIII and X to XIII) of d , k ‐progesterone is described. The chemical transformations of the substituents on rings C and D are largely governed by neighbouring group interference. This is shown by the formation of the cyclic ether XVI, by the unusual acetylation of an 11β‐hydroxy group (IV → VII, VIII), and by the easy ester hydrolysis (X → XII), possibly through anchimeric intervention.