title: Double annulative cascade of tryptophan-containing peptides triggered by selectfluor.
abstract: A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic α-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the α-carboline fragment.
authors: Department of Chemistry and Biochemistry, Florida Atlantic University , Physical Science Building, 777 Glades Road, Boca Raton, Florida 33431, United States.
authors: Bret
authors: B
authors: Tréguier
authors: Stéphane P
authors: SP
authors: Roche
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D003979:Diazonium Compounds / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D001688:Biological Products; D003979:Diazonium Compounds; D026121:Indole Alkaloids; D009842:Oligopeptides; D010456:Peptides, Cyclic; C522312:chaetominine; C541864:kapakahine B; C476160:kapakahine F; C408750:selectfluor; D014364:Tryptophan