A NOVEL CHEMICAL SYNTHESIS AND C-13 NUCLEAR-MAGNETIC-RESONANCE SPECTRAL PROPERTIES OF CHOLEST-4-ENE-3,6-DIONE

This paper presents a novel method for the chemical synthesis of chole st-4-ene-3,6-dione, which is a naturally occurring steroid and a poten tial intermediate in steroid chemistry. Pyridinium chlorochromate (PCC ) in refluxing benzene has been found to be an effective and convenien t reagent for the oxidation and concomitant isomerization of cholest-D elta'-en-3 beta-ol 3-tetrahydropyranyl ether (cholesterol tetrahydropy ranyl ether) to cholest-4-ene-3,6-dione in high yield. Also described are the carbon-13 nuclear magnetic resonance spectral properties of ch olest-4-ene-3,6-dione.