title: Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate.
abstract: 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.
authors.affiliation: The Division of Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, United States.
authors.forename: Yi
authors.initials: Y
authors.lastname: Kou
authors.forename: Myong Chul
authors.initials: MC
authors.lastname: Koag
authors.forename: Young
authors.initials: Y
authors.lastname: Cheun
authors.forename: Aram
authors.initials: A
authors.lastname: Shin
authors.forename: Seongmin
authors.initials: S
authors.lastname: Lee
mesh_terms: D000588:Amines / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004144:Diosgenin / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D017613:Iodine Compounds / Q000737:chemistry; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis*; D013256:Steroids / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D000970:Antineoplastic Agents; D005609:Free Radicals; D017613:Iodine Compounds; D012991:Solanaceous Alkaloids; D013256:Steroids; C081961:hypoiodous acid; D004144:Diosgenin; C012037:solasodine