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Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products.
Org Lett. 2015 Jul 17; 17(14):3446-9.OL

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Naresh G
†Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
Kant R
†Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
Narender T
†Medicinal and Process Chemistry Division and ‡Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.

MeSH

AlkynesAntineoplastic AgentsBenzodioxolesBiological ProductsCatalysisDioxolanesLignansMolecular StructureNaphthalenesNaphtholsSilverStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26158760

Citation

Naresh, Gunaganti, et al. "Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application Toward Expeditious Synthesis of Lignan Natural Products." Organic Letters, vol. 17, no. 14, 2015, pp. 3446-9.
Naresh G, Kant R, Narender T. Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products. Org Lett. 2015;17(14):3446-9.
Naresh, G., Kant, R., & Narender, T. (2015). Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products. Organic Letters, 17(14), 3446-9. https://doi.org/10.1021/acs.orglett.5b01477
Naresh G, Kant R, Narender T. Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application Toward Expeditious Synthesis of Lignan Natural Products. Org Lett. 2015 Jul 17;17(14):3446-9. PubMed PMID: 26158760.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products. AU - Naresh,Gunaganti, AU - Kant,Ruchir, AU - Narender,Tadigoppula, Y1 - 2015/07/09/ PY - 2015/7/10/entrez PY - 2015/7/15/pubmed PY - 2015/10/30/medline SP - 3446 EP - 9 JF - Organic letters JO - Org Lett VL - 17 IS - 14 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26158760/Silver_I__Catalyzed_Regioselective_Construction_of_Highly_Substituted_α_Naphthols_and_Its_Application_toward_Expeditious_Synthesis_of_Lignan_Natural_Products_ DB - PRIME DP - Unbound Medicine ER -