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Configurational assignment by 13C NMR of stereoisomeric 3-bromo-3-acyl derivatives of 5α- and 5β- androstane

✍ Scribed by J. P. Bégué; D. Bonnet-Delpon

Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
258 KB
Volume
18
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The configurational assignment of stereoisomeric 3‐bromo‐3‐acyl derivatives of steroids in both the 5α and 5β series has been carried out by comparing the ^13^C chemical shifts of C‐3. A downfield shift is observed for C‐3, bearing a bromine and an acyl group, on going from the isomer with an equatorial bromine to that with an axial bromine. This rule has been established by comparison of the ^13^C chemical shifts of model compounds in 4‐tert‐butylcyclohexanes of known configuration.

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