title: Total synthesis of N-methylwelwitindolinone D isonitrile.
abstract: Described is a concise total synthesis of N-methylwelwitindolinone D isonitrile, the first in a family of complex bicyclo[4.3.1]decane-containing indole alkaloids to yield to synthesis. The complete carbon core of the natural product was assembled rapidly through a Lewis acid-mediated alkylative coupling followed directly by a palladium-catalyzed enolate arylation reaction. The final ring of the pentacycle was introduced by an indole oxidation/cyclization, and the isonitrile was installed through the rearrangement of an aldehyde to an isothiocyanate followed by desulfurization.
authors: Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, United States.
authors: Vikram
authors: V
authors: Bhat
authors: Kevin M
authors: KM
authors: Allan
authors: Viresh H
authors: VH
authors: Rawal
mesh_terms: D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D010165:Palladium