TY - JOUR
T1 - 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
AU - Spike, Thomas E.
AU - Martin, Joseph A.
AU - Huntoon, Steven
AU - Wang, Andrew HC
AU - Knapp, Furn F.
AU - Schroepfer, George J.
N1 - Funding Information:
This work was supported in part by grants from the National Institutes of ttea!th (HL.O9501 and HL-15376), the Robert A. Welch Foundation ~d the Illinois Heart Association. T.E.S. w~ supported by a National Institutes of Health Predoctoral Traineeship. We ",dso wish to acknowledge the advice and encouragement of Professor !.C. Paul in the X-ray crystallographic studies.
PY - 1978/4
Y1 - 1978/4
N2 - 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.
AB - 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.
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U2 - 10.1016/0009-3084(78)90053-1
DO - 10.1016/0009-3084(78)90053-1
M3 - Article
C2 - 668029
AN - SCOPUS:0017953494
SN - 0009-3084
VL - 21
SP - 31
EP - 58
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
IS - 1-2
ER -