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Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.
Angew Chem Int Ed Engl. 2019 02 11; 58(7):2144-2148.AC

Abstract

To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsaturated carboxylic acid anhydrides. Compared to the previous indenone-preparation approaches, this method allows simple aryl iodides to be used as substrates with complete control of the regioselectivity. The total synthesis of acredinone A features two different Pd/NBE-catalyzed ortho acylation reactions for constructing penta-substituted arene cores, including the development of a new ortho acylation/ipso borylation.

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Authors+Show Affiliations

Liu F
Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA. Department of Applied Chemistry, China Agricultural University, Beijing, 100193, China.
Dong Z
Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
Wang J
Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
Dong G
Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.

MeSH

BenzophenonesCatalysisHydrocarbons, IodinatedIndenesMolecular StructureNorbornanesPalladiumStilbenes

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30600880

Citation

Liu, Feipeng, et al. "Palladium/Norbornene-Catalyzed Indenone Synthesis From Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A." Angewandte Chemie (International Ed. in English), vol. 58, no. 7, 2019, pp. 2144-2148.
Liu F, Dong Z, Wang J, et al. Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A. Angew Chem Int Ed Engl. 2019;58(7):2144-2148.
Liu, F., Dong, Z., Wang, J., & Dong, G. (2019). Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A. Angewandte Chemie (International Ed. in English), 58(7), 2144-2148. https://doi.org/10.1002/anie.201813699
Liu F, et al. Palladium/Norbornene-Catalyzed Indenone Synthesis From Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A. Angew Chem Int Ed Engl. 2019 02 11;58(7):2144-2148. PubMed PMID: 30600880.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A. AU - Liu,Feipeng, AU - Dong,Zhe, AU - Wang,Jianchun, AU - Dong,Guangbin, Y1 - 2019/01/16/ PY - 2018/12/01/received PY - 2019/1/3/pubmed PY - 2020/8/6/medline PY - 2019/1/3/entrez KW - acredinone A KW - indenone KW - norbornene KW - palladium KW - pauciflorol F SP - 2144 EP - 2148 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 7 N2 - To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsaturated carboxylic acid anhydrides. Compared to the previous indenone-preparation approaches, this method allows simple aryl iodides to be used as substrates with complete control of the regioselectivity. The total synthesis of acredinone A features two different Pd/NBE-catalyzed ortho acylation reactions for constructing penta-substituted arene cores, including the development of a new ortho acylation/ipso borylation. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30600880/Palladium/Norbornene_Catalyzed_Indenone_Synthesis_from_Simple_Aryl_Iodides:_Concise_Syntheses_of_Pauciflorol_F_and_Acredinone_A_ DB - PRIME DP - Unbound Medicine ER -