Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization
We developed a method employing stoichiometric meta -chloroperbenzoic acid ( m -CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination-dearomatization of phenols, leading to a range of fluorocy...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2022-10, Vol.2 (41), p.814-817 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Cao, Jiaqi Deng, Qingfu Hu, Liangzhen Zhang, Xiaohui Xiong, Yan |
| description | We developed a method employing stoichiometric
meta
-chloroperbenzoic acid (
m
-CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination-dearomatization of phenols, leading to a range of fluorocyclohexa-dienones with yields of up to 94%. This reaction provides a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. These analogs have potential application as inhibitors of DNA polymerase.
We developed a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. |
| doi_str_mv | 10.1039/d2ob01582j |
| format | Article |
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meta
-chloroperbenzoic acid (
m
-CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination-dearomatization of phenols, leading to a range of fluorocyclohexa-dienones with yields of up to 94%. This reaction provides a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. These analogs have potential application as inhibitors of DNA polymerase.
We developed a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob01582j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Analogs ; DNA polymerase ; DNA-directed DNA polymerase ; Fluorides ; Fluorination ; Fluorine ; Hydrogen fluoride ; Iodine ; Oxidants ; Oxidizing agents ; Phenols ; Reagents</subject><ispartof>Organic & biomolecular chemistry, 2022-10, Vol.2 (41), p.814-817</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c244t-6df4560744a02bb1100a7709feed9dd21577808f95382af22e7577fc5abd89473</citedby><cites>FETCH-LOGICAL-c244t-6df4560744a02bb1100a7709feed9dd21577808f95382af22e7577fc5abd89473</cites><orcidid>0000-0002-5258-5325</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Cao, Jiaqi</creatorcontrib><creatorcontrib>Deng, Qingfu</creatorcontrib><creatorcontrib>Hu, Liangzhen</creatorcontrib><creatorcontrib>Zhang, Xiaohui</creatorcontrib><creatorcontrib>Xiong, Yan</creatorcontrib><title>Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization</title><title>Organic & biomolecular chemistry</title><description>We developed a method employing stoichiometric
meta
-chloroperbenzoic acid (
m
-CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination-dearomatization of phenols, leading to a range of fluorocyclohexa-dienones with yields of up to 94%. This reaction provides a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. These analogs have potential application as inhibitors of DNA polymerase.
We developed a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents.</description><subject>Analogs</subject><subject>DNA polymerase</subject><subject>DNA-directed DNA polymerase</subject><subject>Fluorides</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Hydrogen fluoride</subject><subject>Iodine</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Phenols</subject><subject>Reagents</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0c1LwzAYBvAiCs7pxbsQ8CJCNUnTpj3q_Gawg3ouaT7WjCzZklTo_nrrJhM8hDe8_HggT5LkHMEbBLPqVmDXQJSXeHGQjBChNIV5Vh3u7xgeJychLCBEFS3IKFm_9za2MugAnALKdM5ry6IUYOVMz3tuNAdCtr3wjpkobRe0Bcwy4-YBxNa7bt6Ctl9J_8WMtBFoJ7SVKWeRmX4zBAnJvFuyqDfDcfY0OVLMBHn2O8fJ59Pjx-Qlnc6eXyd305RjQmJaCEXyAlJCGMRNgxCEjFJYKSlFJQRGOaUlLFWVZyVmCmNJh43iOWtEWRGajZOrXe7Ku3UnQ6yXOnBpDLPSdaHGFGdDSIXLgV7-owvX-eGNW1WSHMECD-p6p7h3IXip6pXXS-b7GsH6p_36Ac_ut-2_Dfhih33ge_f3O9k3M6eD1Q</recordid><startdate>20221026</startdate><enddate>20221026</enddate><creator>Cao, Jiaqi</creator><creator>Deng, Qingfu</creator><creator>Hu, Liangzhen</creator><creator>Zhang, Xiaohui</creator><creator>Xiong, Yan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5258-5325</orcidid></search><sort><creationdate>20221026</creationdate><title>Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization</title><author>Cao, Jiaqi ; Deng, Qingfu ; Hu, Liangzhen ; Zhang, Xiaohui ; Xiong, Yan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c244t-6df4560744a02bb1100a7709feed9dd21577808f95382af22e7577fc5abd89473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Analogs</topic><topic>DNA polymerase</topic><topic>DNA-directed DNA polymerase</topic><topic>Fluorides</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Hydrogen fluoride</topic><topic>Iodine</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Phenols</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cao, Jiaqi</creatorcontrib><creatorcontrib>Deng, Qingfu</creatorcontrib><creatorcontrib>Hu, Liangzhen</creatorcontrib><creatorcontrib>Zhang, Xiaohui</creatorcontrib><creatorcontrib>Xiong, Yan</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cao, Jiaqi</au><au>Deng, Qingfu</au><au>Hu, Liangzhen</au><au>Zhang, Xiaohui</au><au>Xiong, Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2022-10-26</date><risdate>2022</risdate><volume>2</volume><issue>41</issue><spage>814</spage><epage>817</epage><pages>814-817</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We developed a method employing stoichiometric
meta
-chloroperbenzoic acid (
m
-CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination-dearomatization of phenols, leading to a range of fluorocyclohexa-dienones with yields of up to 94%. This reaction provides a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. These analogs have potential application as inhibitors of DNA polymerase.
We developed a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2ob01582j</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-5258-5325</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2022-10, Vol.2 (41), p.814-817 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2723157928 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Analogs DNA polymerase DNA-directed DNA polymerase Fluorides Fluorination Fluorine Hydrogen fluoride Iodine Oxidants Oxidizing agents Phenols Reagents |
| title | Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization |
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