A sterospecific synthesis of 7alpha-hydroxycholesterol.
The five step synthesis of 7alpha-hydroxycholesterol utilizes the solvolysis of 7alpha-bromocholesterol benzoate with potassium acetate in acetic acid as the key step in controlling the stereospecificity of the reaction sequence. This reaction yields 7alpha-acetoxycholesterol benzoate with retention of configuration at position seven. The diester is readily reduced with lithium aluminum to 7alpha-hydroxycholesterol.
D006888:Hydroxycholesterols / Q000138:chemical synthesis*; D008722:Methods; D008968:Molecular Conformation
D006888:Hydroxycholesterols