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.

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► 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.