title: Discovery of hypoiodite-mediated aminyl radical cyclization lacking a nitrogen radical-stabilizing group: application to synthesis of an oxazaspiroketal-containing cephalostatin analog.
abstract: Synthesis of an oxazaspiroketal-containing bissteroidal pyrazine is described. The key transformation of this synthesis involves stereoselective formation of oxazaspiroketal via aminyl-radical cyclization of primary amine lacking a radical-stabilizing group by Suárez hypoiodite oxidation.
authors.affiliation: The Division of Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Texas 78712, USA.
authors.forename: Myong
authors.initials: M
authors.lastname: Koag
authors.forename: Seongmin
authors.initials: S
authors.lastname: Lee
mesh_terms: D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D017613:Iodine Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D005609:Free Radicals; D017613:Iodine Compounds; D013141:Spiro Compounds; D013256:Steroids; C081961:hypoiodous acid; D009584:Nitrogen