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Ein neuer Reaktionsweg zu 1, 3-Dicarbonylderivaten. Modelluntersuchungen am A/B-Teil von 3-Oxo-5α-steroiden

✍ Scribed by Hans Berbalk; Karl Eichinger; Willibald Winetzhammer


Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
377 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis


A New Route to 1, 3‐Dicarbonyl Derivatives, Model Investigations on the A/B‐Part of‐3‐Oxo‐5α‐steroids

Starting from 1 the 1, 3‐dicarbonyl compounds 4ad were synthetized via the enynes 2ae and the relatively unstable epoxides 3ad. The latter were reacted with 95% formic acid to gave 4ad; small amounts of the furane derivatives 5ac were identified as by‐products in this last step. In the presence of catalytic amounts of HgSO~4~ the epoxides 3ac yielded with 95% formic acid the furanes 5ac, but no detectable amounts of 4ac.


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✍ Frl. E. Gössinger; W. Graf; R. Imhof; H. Wehrli 📂 Article 📅 1971 🏛 John Wiley and Sons 🌐 German ⚖ 291 KB 👁 1 views

## Abstract A novel method for the reductive epoxide opening in a 14β, 15β‐epoxy‐20‐oxo‐Δ^16^‐pregnene **4** affords an almost quantitative yield of the 14β‐hydroxy‐20‐oxo‐Δ^16^‐pregnene **5.** This leads to a considerable improvement of the formerly published synthesis of 3‐O‐methyl 17 α, 20ξ‐tetr