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Über Steroide und Sexualhormone. 225. Mitteilung. UV.-Bestrahlung von 11-Oxo-Steroiden II Die Darstellung von Δ4- und Delta;5-11β, 19-Cyclo-pregnen- sowie 5β-11β, 19-Cyclo- und 5, 19-Cyclo-pregnan-Verbindungen

✍ Scribed by M. S. Heller; H. Wehrli; K. Schaffner; O. Jeger

Publisher: John Wiley and Sons
Year: 1962
Tongue: German
Weight: 962 KB
Volume: 45
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19620450423

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✦ Synopsis

Abstract

In analogy to the previously described photochemical isomerisation of 3,20‐diethylenedioxy‐11‐oxo‐5 α‐pregnane (I → II) the UV.‐irradiation of the Δ^5^‐ and 5β‐11‐oxo‐steroids III and XXII gives rise to the 11 α‐hydroxy‐11, 19‐cyclo derivatives IV and XXIII, respectively. The observed yields of these tertiary cyclobutanol products decrease in the order II > IV > XXIII. The possible significance of these structure‐dependent rate differences is discussed.

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Über Steroide und Sexualhormone. 223. Mi

Über Steroide und Sexualhormone. 223. Mitteilung. UV.-Bestrahlung von 11-Oxo-Steroiden I Die Darstellung von 11β, 19-Cyclo-, 9β, 19-Cyclo- und 19-Hydroxy-5α-pregnan-Verbindungen

✍ H. Wehrli; M. S. Heller; K. Schaffner; O. Jeger 📂 Article 📅 1961 🏛 John Wiley and Sons 🌐 German ⚖ 785 KB

1. A new two‐step process for the functionalisation of the non‐activated methyl group 19 of 5α‐steroids is described. In the first step UV.‐irradiation of the 11‐oxo‐5α‐pregnane derivate I in ethanol gives rise to a preferential attack of the photochemically excited carbonyl on methyl group 19, lead