The reductive cleavage of the ether bridge of 5α-chloro- and 5α-bromo-6β, 19-oxido-steroids to 19-hydroxy-Δ5-steroids has been studied : Whereas 5α-bromo-6β, 19-ethers could be reduced under mild conditions, i. e. with zinc and acetic acid, 5α-chloro-6β, 19-ethers could only be cleaved with lithium and liquid ammonia. However, the latter steroids with an additional electronegative substituent in 19-position, namely 5α-chloro-6β, 19-hemiacetals and -lactones, were smoothly converted into Δ5-19-aldehydes and Δ5-19-acids, respectively, by the action of zinc and acetic acid. The Δ5-steroid-3 9-oic acids obtained could be decarboxylated thermally to Δ5(10)-19-norsteroids.

19‐Norsteroide IV. Über die reduktive Ätherspaltung bei 5α‐Halogen‐6β, 19‐oxido‐steroiden. Über Steroide, 198. Mitteilung

The skeletal rearrangement of α-halogeno-ketones, which is known as the Favorskii rearrangement, is met most frequently in aliphatic monocyclic, and polycyclic halogenated ketones. This molecular rearrangement is used in the synthesis of branched carboxylic acids and cis-αβ-unsaturated acids and for obtaining smaller rings in alicyclic and to a less extent heterocyclic compounds. The sterochemistry and the mechanism of the Favorskii rearrangement are also considered, these being of great interest for theoretical organic chemistry. A list of 261 references is included.

https://iopscience.iop.org/article/10.1070/RC1970v039n09ABEH002019/pdf

The Favorskii Rearrangement

Aus den Arbeiten der letzten zwei Jahre auf dem Gebiet der Nebennierenrinden-Hormone stechen — was die Herstellung neuer, hochwirksamer Verbindungen anbetrifft — die Isolierung und Konstitutionsaufklarung des naturlichen Hormons Aldosteron und die synthetische Gewinnung der 9α-halogenierten Hydrocortisone hervor. Diese Ergebnisse haben den Weg zu weiteren wesentlichen Entwicklungen eines Gebietes geoffnet, das mit Cortison und Hydrocortison abgeschlossen schien.

Advances in the field of adrenal cortical hormones.

The stereochemistry of reactions of nucleophilic addition to the carbonyl group of cyclic ketones

Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)

809. Modified steroid hormones. Part IV. 6-Methylpregnane derivatives

811. Modified steroid hormones. Part VI. Further 6-methyl-androstane derivatives

810. Modified steroid hormones. Part V. 6-Methylandrostane derivatives

864. 4 : 4-Dimethylsteroids. Part II. Some androstane and pregnane derivatives

61. 16-Oxo- and 16α-hydroxy-testosterone

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