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Carbon-13 NMR spectra of steroidal epoxides. Configurational assignment of an epoxy group on six-membered ring by carbon-13 NMR spectroscopy

✍ Scribed by Kazuo Tori; Taichiro Komeno; M. Sangaré; B. Septe; B. Delpech; A. Ahond; G. Lukacs

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
239 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the structure elucidation of epoxide-containing natural produck,' we have been confronted with the problem of assignment of configuration of the three-membered ring. Although the relatively high field resonance of epoxide carbons has already been noticed,3 no systematic study has been made on the influence of an epoxide ring on the chemical shifts of neighbouring carbons. We report here 13C NMR shift correlations of various steroidal A-ring epoxides and demonstrate the utility of this technique for the assignment of configuration of a three-membered ring of this type.

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✍ Braja G. Hazra; Vandana S. Pore; Padmakar L. Joshi; Sharmila N. Padalkar; Shubha 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 404 KB

## Abstract Stereoisomers of steroidal 22‐hydroxy‐23‐acetylenic, 23‐olefinic and 23, 24‐isomeric epoxides were synthesized from C‐22 aldehydes and their ^13^C NMR spectra were analysed. A correlation regarding the combined effect of the 22‐hydroxy and 23, 24‐substituents on the stereochemistry of t