A convenient protocol for the synthesis of A-ring lactones derived from cholesterol
was developed. A lactone reduction–lactol separation–reoxidation sequence, applied
to the inseparable mixture of diastereomeric lactones, allows the production of multigram
amounts of each lactone in pure form. The same sequence applied to A-ring lactones
derived from diosgenin produced similar results. A detailed NMR characterization of
all the obtained lactones is also provided. X-ray diffraction corroborated the structure
of the obtained compounds.
Key words
steroids - epimeric lactones - lactols - NMR analysis - X-ray diffraction
