title: Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.
abstract: We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
authors.forename: Kyle W
authors.initials: KW
authors.lastname: Quasdorf
authors.forename: Alexander D
authors.initials: AD
authors.lastname: Huters
authors.forename: Michael W
authors.initials: MW
authors.lastname: Lodewyk
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry; D006900:Hydroxylation; D008958:Models, Molecular; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; C092269:N-methylwelwitindolinone C nitrile