Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate

Solasodine acetate, an anticancer steroidal alkaloid, was synthesized from diosgenin in 8 steps with an overall yield of 23%. A key synthetic step involves the formation of 5/6-oxazaspiroketal moiety via hypoiodite-mediated aminyl radical cyclization of a steroidal primary amine.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Application of hypoiodite-mediated aminyl radical cyclization to synthesis of a steroidal alkaloid. ► A mild, stereoselective method for 5/6-oxazaspiroketal formation. ► Efficient synthesis of solasodine acetate via “Red-Ox” modifications of diosgenin.