PMID: 9178427May 1, 1997Paper

7 beta-hydroxy bile alcohols: facile synthesis and 2D 1H NMR studies of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol

Steroids
B DayalG Salen

Abstract

A rapid and easily performed procedure for the synthesis of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol by means of an efficient homologation sequence of the intermediate, 3 alpha, 7 beta, 12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane is described. The reaction sequence involved treating the intermediate, alpha-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homourscholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol in 88% yield. The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism.

References

Apr 1, 1976·The Journal of Clinical Investigation·S SheferE H Mosbach
Jan 1, 1979·The Journal of Clinical Investigation·G SalenG S Tint

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