A facile chemical synthesis of cholest‐4‐en‐3‐one. Carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and cholest‐5‐en‐3‐one

This paper presents a simplified method for the chemical synthesis of cholest‐4‐en‐3‐one, which is a naturally occurring steroid and a salient intermediate in steroid chemistry. Pyridinium chlorochromate (PCC) in refluxing benzene has been found to be an effective and convenient reagent for the oxid...

Full description

Saved in:
Bibliographic Details
Published inLipids Vol. 26; no. 8; pp. 675 - n/a
Main Authors Parish, Edward J, Honda, Hiroshi, Chitrakorn, Sarawanee, Livant, Peter
Format Journal Article
LanguageEnglish
Published Berlin/Heidelberg Springer‐Verlag 01.08.1991
Springer
Subjects
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Other biological molecules
Lipids
NMR spectrometry
Online AccessGet full text

Cover

More Information
Summary:This paper presents a simplified method for the chemical synthesis of cholest‐4‐en‐3‐one, which is a naturally occurring steroid and a salient intermediate in steroid chemistry. Pyridinium chlorochromate (PCC) in refluxing benzene has been found to be an effective and convenient reagent for the oxidation and concomitant isomerization of cholest‐5‐en‐3β‐ol (cholesterol) to cholest‐4‐en‐3‐one in high yield. Also described are the carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and of the isolated reaction intermediate cholest‐5‐en‐3‐one.
Bibliography:Based on a paper presented at the Symposium on Plant and Fungal Sterols: Biosynthesis Metabolism and function held at the AOCS Annual Meeting, Baltimore, MD, April 1990.
ISSN:0024-4201
1558-9307
DOI:10.1007/BF02536435