New bile alcohols - synthesis of 5β cholestane 3α,7α, 3α,7α,25 and 5β cholestane 3α,7α,25-24(14C) triol

Article abstract of DOI:10.1016/0039-128X(75)90093-8

5β Cholestane 3α,7α,25 triol and 5β cholestane 3α,7α,24-25(¹⁴C) triol were synthesized from 3α,7α dihydroxy 5β cholanoic acid (chenodeoxycholic acid). Chenodeoxycholic acid was converted to the diformoxy derivative (II) using formic acid. Reaction of II with thionyl chloride yielded the acid chloride which was treated with diazomethane (CH₂N₂ or ¹⁴CH₂N₂) to produce 3α,7α diformoxy 24 oxo 25 diazo 25 homocholane (III, A or B). 25 Homochenodeoxycholic acid (IV A or B) was formed from III by means of the Wolff rearrangement of the Arndt Eistert synthesis. The methyl ester of V (A or B) was treated with methyl magnesium iodide in ether to provide the desired triol, VI (A and B). The triol was identified by mass spectrometry and elemental analysis and was characterized by thin layer and gas liquid chromatography. The 3α,7α,25 triol is of possible significance as an intermediate in the pathway of bile acid formation from cholesterol.