title: Progress toward the total synthesis of N-methylwelwitindolinone B isothiocyanate.
abstract: Progress toward the welwitindolinone alkaloid N-methylwelwitindolinone B isothiocyanate is reported. A key reaction to synthesize the [4.3.1] bicycle embedded in the core of the molecule is a furan type 2 intramolecular Diels-Alder reaction with a tetrasubstituted dienophile, which sets the two vicinal quaternary centers present in the natural product. The sterically encumbered cycloaddition precursor was synthesized using a Horner-Wadsworth-Emmons reaction followed by a Suzuki cross-coupling reaction. Finally, introduction of the secondary alkyl chloride was achieved by a regio- and diastereoselective opening of a [2.2.1] oxobicycloheptane functionality.
authors.affiliation: Department of Chemistry, University of California, Irvine , 1102 Natural Sciences 2, Irvine, California 92697-2025, United States.
authors.forename: Leah
authors.initials: L
authors.lastname: Cleary
authors.forename: Jennifer
authors.initials: J
authors.lastname: Pitzen
authors.forename: John A
authors.initials: JA
authors.lastname: Brailsford
authors.forename: Kenneth J
authors.initials: KJ
authors.lastname: Shea
mesh_terms: D000458:Cyanobacteria / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D026121:Indole Alkaloids; C000598265:N-methylwelwitindolinone B isothiocyanate; C560824:welwitindolinone B isothiocyanate