On the Synthesis of Scymnol

Abstract

Reinvestigation of a reported synthesis of scymnol (5β-cholestane-3α,7α,12α,24,26,27-hexol) has cast doubt on the success of that synthetic route. A modified synthetic pathway has been developed and scymnol, racemic at C24, has been unequivocally prepared from cholic acid. Extensive proton and ¹³C n.m.r. spectroscopy has been used to confirm the structure of the product. A new, simple method of desulfation of natural scymnol sufate has been developed.