Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14 alpha-methyl-5 alpha-cholest-7-en-3 beta, 15 beta-diol and 14 alpha-methyl-5 alpha-cholest-7-en-3 beta, 15 alpha-diol

Abstract

14alpha-Methyl-5alpha-cholest-7-en-3beta,15beta-diol and 14alpha-methyl-5alpha-cholest-7-en-3beta,15alpha-diol have been prepared by chemical synthesis. Unequivocal establishment of these structures was based upon X-ray crystallographic analysis of 3beta-p-bromobenzoyloxy-14alpha-methyl-5alpha-cholest-7-en-15beta-ol and was supported by other spectroscopic data. Spectroscopic data were presented for the following compounds prepared in this study: 3beta-benzoyloxy-5alpha-cholest-8(14)-en-15-one, 3beta-benzoyloxy-14alpha-methyl-5alpha-cholest-7-en-15-one, 3beta-benzoyloxy-14alpha-methyl-5alpha-cholest-7-en-15beta-ol, 14alpha-methyl-5alpha-cholest-7-en-3beta, 15beta-diol, 14alpha-methyl-5alpha-cholest-7-en-3beta, 15alpha-cholest-7-en-15beta-diol, 14alpha-methyl-5alpha-cholest-7-en-3beta, 15alpha-diol, 3beta, 15alpha-bis-benzoyloxy-14alpha-methyl-5alpha-cholest-7-ene, 3beta-p-bromobenzoyloxy-14alpha-methyl-5alpha-cholest-7-en-15beta-ol and 3beta, 15beta-bis-p-bromobenzoyloxy-14alpha-methyl-5alpha-cholest-7-ene. Studies of the metabolism of [16-3H]-14alpha-methyl-5alpha-cholest-7-en-3beta, 15beta-diol and [16-3H]-14 alpha-methyl-5 alpha-cholest-7-en-3beta, 15alpha-diol in liver homogenates of female rats indicated that only the 3beta, 15beta-diol was convertible to cholesterol.