Sterol synthesis. Chemical synthesis of 3beta-benzoyloxy -14alpha, 15alpha-epoxy-5alpha-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols.
3BETA-Benzoyloxy-14alpha, 15alpha-cholest-7-ene was obtained in 96% yield upon treatment of 3beta-benzoyloxy-5alpha-cholesta-7, 14-diene with m-chloroperbenzoic acid. The delta7-14alpha, 15alpha-epoxy-steryl ester provides a useful intermediate for the syntheses of sterols with an oxygen function at carbon atom 15. For example, treatment of 3beta-benzoyloxy-14alpha, 15alpha-epoxy-5alpha-cholest-7-ene with methanolic hydrochloric acid gave 3beta-benzoyloxy-5alpha-cholest-8(14)-en-15-one in 82% yield.
D002782:Cholestenes / Q000138:chemical synthesis*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008722:Methods; D013055:Spectrophotometry, Infrared
D002782:Cholestenes; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D007202:Indicators and Reagents