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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Syntheses of ring C oxysterols: inhibitors of sterol biosynthesis
Edward J Parish1, Chi Luo, Thomas Webb
1Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 336849, USA, parisej@auburn.edu
Abstract:
Oxygenated derivates of cholesterol and lanosterol, known as oxysterols, have consistently displayed significant activity as inhibitors of 3-hydroxy-3-methylglutaryl (HMG) CoA reductase, a key regulatory enzyme in sterol biosynthesis. We have developed the chemical syntheses of ring C oxysterols for evaluation as inhibitors of sterol biosynthesis. A key intermediate in the chemical synthesis was 3beta-benzoyloxy-9alpha, 1alpha-epoxy-5alpha-cholest-7-ene (1), whose structure was confirmed by X-ray crystallographic analysis and is presented herein.
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