title: Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products.
abstract: A novel route has been developed for regioselective synthesis of highly substituted α-naphthols, binaphthols, and anthracenol through silver(I) catalyzed C(sp(3))-H/C(sp)-H, C(sp(2))-H/C(sp)-H functionalization of β-ketoesters and alkynes, respectively, in a single step using water as a solvent. This protocol exhibited broad substrate scope and paved the way for synthesis of anticancer arylnaphthalene lignan natural products such as diphyllin, taiwanin E, and justicidin A with excellent selectivity.
authors.affiliation: †Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
authors.forename: Gunaganti
authors.initials: G
authors.lastname: Naresh
authors.affiliation: †Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
authors.forename: Ruchir
authors.initials: R
authors.lastname: Kant
authors.affiliation: †Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
authors.forename: Tadigoppula
authors.initials: T
authors.lastname: Narender
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D052117:Benzodioxoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D052117:Benzodioxoles; D001688:Biological Products; D004148:Dioxolanes; D017705:Lignans; D009281:Naphthalenes; D009284:Naphthols; C049719:justicidins; C000602275:taiwanin E; C029350:1-naphthol; D012834:Silver; C010130:diphyllin