title: Formal syntheses of naturally occurring welwitindolinones.
abstract: The formal syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, N-methylwelwitindolinone D isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate, and 3-hydroxy-N-methylwelwitindolinone C isonitrile are reported. The synthesis features several novel processes, including a Lewis acid mediated coupling between a benzylic-type heteroaromatic alcohol and a highly functionalized silyl ketene acetal, an intramolecular enolate arylation, and a regioselective, Pd(0)-catalyzed π-allylic cyclization of a γ-benzoyloxy enone moiety that is revealed by unmasking a furan ring.
authors: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors: Tsung-hao
authors: TH
authors: Fu
authors: William T
authors: WT
authors: McElroy
authors: Mariam
authors: M
authors: Shamszad
authors: Stephen F
authors: SF
authors: Martin
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; D058116:Lewis Acids; C092268:N-methylwelwitindolinone C isothiocyanate