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Über eine homolytische Wasserstoffverschiebung in einem Cyclohexanring. Über Steroide, 201. Mitteilung

✍ Scribed by K. Heusler; J. Kalvoda

Publisher
John Wiley and Sons
Year
1963
Tongue
German
Weight
809 KB
Volume
46
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The homolytic cleavage of the 5,6‐bond initiated by treatment of 3β,20β‐di‐acetoxy‐6α‐methyl‐6β‐hydroxy‐5α‐pregnane with lead tetraacetate is followed by a transannular homolytic hydrogen transfer from C‐1 to C‐5, rotation of ring A around the C‐9/C‐10 bond and recyclisation to a pregnane with an inverted 10‐methyl group. The rearranged product has been converted into 6α‐methyl‐10α‐progesterone, which was then transformed into its 1‐dehydro derivative. The course of the reaction was investigated by specific deuterium labelling.

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✍ K. Heusler; J. Kalvoda; G. Anner; A. Wettstein 📂 Article 📅 1963 🏛 John Wiley and Sons 🌐 German ⚖ 878 KB

## Abstract The lead ester formed from steroidal alcohols with lead tetraacetate are thermally decomposed to oxy radicals which can either form tetrahydrofurane derivatives by direct attack on a hydrogen atom at δ‐carbon atom or, by cleavage of the α,β‐carbon bond, give rise to a carbonyl group and