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

Thomas E. Spike, Joseph A. Martin, Steven Huntoon, Andrew HC Wang, Furn F. Knapp, George J. Schroepfer

Research output: Contribution to journalArticlepeer-review

Abstract

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

Original languageEnglish
Pages (from-to)31-58
Number of pages28
JournalChemistry and Physics of Lipids
Volume21
Issue number1-2
DOIs
Publication statusPublished - Apr 1978
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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