Reinvestigation of a reported synthesis of scymnol a-cholestane-3alpha
,7alpha,12alpha,24,26,27-hexol) has cast doubt on the success of that
synthetic route. A modified synthetic pathway has been developed and s
cymnol, racemic at C24, has been unequivocally prepared from cholic ac
id. Extensive proton and C-13 n.m.r. spectroscopy has been used to con
firm the structure of the product. A new, simple method of desulfation
of natural scymnol sufate has been developed.