title: Total synthesis of (-)-N-methylwelwitindolinone B isothiocyanate via a chlorinative oxabicycle ring-opening strategy.
abstract: The first total synthesis of N-methylwelwitindolinone B isothiocyanate is reported. The route features several key steps, including a regio- and diastereoselective chlorinative oxabicycle ring-opening reaction to introduce the challenging alkyl chloride motif.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Weires
authors.forename: Evan D
authors.initials: ED
authors.lastname: Styduhar
authors.forename: Emma L
authors.initials: EL
authors.lastname: Baker
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D054879:Halogenation; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D017879:Isothiocyanates / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D026121:Indole Alkaloids; D017879:Isothiocyanates; C560824:welwitindolinone B isothiocyanate; C037152:isothiocyanic acid