Synthesis of 3β-Hydroxy-5β-pregn-8(14)-en-20-one from Chenodeoxycholic Acid

Article abstract of DOI:10.1002/hlca.19860690810

3β-Hydroxy<21-14C>-5β-pregn-8(14)-en-20-one (17) was prepared from chenodeoxycholic acid (1a).The synthetic sequence involved: i) degradation of the bile-acid side chain to an etianic acid; ii) formation of the 8(14)-double bond;iii) inversion of the configuration at C(3);iv) construction of the acetyl side chain at C(17) with the required isotopic label at C(21).Structures of all described products were confirmed by chemical and spectroscopic (IR,1H-NMR, 13C-NMR,MS) methods.