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Reaktionen von Steroid‐Hypojoditen II. Über die Herstellung 18‐oxygenierter Pregnanverbindungen. Über Steroide, 187. Mitteilung
Author(s) -
Meystre C. H.,
Heusler K.,
Kalvoda J.,
Wieland P.,
Anner G.,
Wettstein A.
Publication year - 1962
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.19620450431
Subject(s) - chemistry , reagent , yield (engineering) , iodine , medicinal chemistry , hemiacetal , steroid , silver acetate , radical , organic chemistry , hormone , biochemistry , materials science , metallurgy
The reactions of 20‐hydroxypregnanes with iodine and lead tetraacetate, mercuric or silver acetate yield the corresponding oxy radicals. With the latter two reagents, 20‐hypoiodites are definitely intermediates. The primary reaction products, i.e. 18‐iodo‐20‐hydroxy compounds, can be oxidized and hydrolized to 18‐hydroxy‐20‐oxo‐pregnanes. Under suitable conditions, especially with lead tetraacetate and iodine, a second substitution reaction on carbon 18 of the 18‐iodo‐20‐hydroxy‐pregnanes takes place, leading to compounds of the (18 → 20)‐hemiacetal type. These can be oxidized to (18 → 20)‐lactones.