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Journal of Lipid Research, Vol 20, 570-578, Copyright © 1979 by Lipid Research, Inc.
ARTICLES |
RA Pascal Jr, R Shaw and GJ Schroepfer Jr
Reported herein are chemical syntheses of 14 alpha-hydroxymethyl-5 alpha-cholest-8-en-3 beta-ol, 14 alpha-hydroxymethyl-5 alph-cholest-7- en-3 beta-ol, and 14 alpha-hydroxymethyl-5 alpha-cholest-6-en 3 beta- ol. These compounds were obtained in pure form after repeated medium- pressure column chromatography of the mixture obtained by treatment of 3 beta-acetoxy-7 alpha,32-epoxy-14 alpha-methyl-5 alpha-cholestane with pyridine hydrochloride in refluxing acetic anhydride followed by reduction with lithium aluminum hydride. The compounds were characterized by their chromatographic properties and by the results of infrared, optical rotation, nuclear magnetic resonance, and low and high resolution mass spectral studies.
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