title: Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.
abstract: The total synthesis of N-methylwelwitindolinone D isonitrile (1) has been achieved in 17 steps from a readily available carvone derivative. The route features a double C-H functionalization event involving a keto oxindole substrate to introduce the tetrahydrofuran ring of the natural product.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 (USA) http://www.chem.ucla.edu/dept/Faculty/garg/Garg_Group/Home.html.
authors.forename: Evan D
authors.initials: ED
authors.lastname: Styduhar
authors.forename: Alexander D
authors.initials: AD
authors.lastname: Huters
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Weires
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003503:Cyclobutanes; D007097:Imines; D026121:Indole Alkaloids; C000588803:N-methylwelwitindolinone D isonitrile; D009570:Nitriles; C017621:phenylnitrene; D002244:Carbon; D006859:Hydrogen
keywords: C-H functionalization; natural products; nitrene insertion; total synthesis; welwitindolinone