title: Ene-hydrazide from enol triflate for the regioselective Fischer indole synthesis.
abstract: Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural β-carboline alkaloid, difficult to prepare with conventional Fischer indole synthesis.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, Hanyang University , 222 Wangshimni-ro, Seongdong-gu, Seoul 133-791, Korea.
authors.forename: Byeong-Yun
authors.initials: BY
authors.lastname: Lim
authors.forename: Bo-Eun
authors.initials: BE
authors.lastname: Jung
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
mesh_terms: D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; D006834:Hydrazines; D026121:Indole Alkaloids; C506148:desbromoarborescidine A