Reaktionen von Steroid‐Hypojoditen II. Über die Herstellung 18‐oxygenierter Pregnanverbindungen. Über Steroide, 187. Mitteilung

Abstract

Abstract 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.