title: Regiodivergent annulation of alkynyl indoles to construct spiro-pseudoindoxyl and tetrahydro-β-carbolines.
abstract: Regiodivergent annulations of 3-phenoxy alkynyl indoles have been developed and tuned by protective groups through gold catalysis. With electron-donating protective groups, the substrate followed a C3-selective annulation and gave structurally interesting tetrahydro-β-carboline derivatives possessing potential bioactivity. Using electron-withdrawing protective groups, the substrate underwent a C2-selective annulation and afforded the structurally useful spiro-pseudoindoxyl found in natural indole alkaloids. Notably, an interesting and unusual 1, 2-migration of the phenoxy group was found in the C3-selective process.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Zhang
authors.forename: Dao-Yong
authors.initials: DY
authors.lastname: Zhu
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Jiao
authors.forename: Bao-Sheng
authors.initials: BS
authors.lastname: Li
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Zhigang
authors.initials: Z
authors.lastname: Bi
mesh_terms: D000478:Alkylation; D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D006046:Gold / Q000737:chemistry; D006865:Hydrogenation; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; D007211:Indoles; D013141:Spiro Compounds; D006046:Gold