Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A
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...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-02, Vol.58 (7), p.2144-2148 |
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| creator | Liu, Feipeng Dong, Zhe Wang, Jianchun Dong, Guangbin |
| description | 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.
A straightforward method for indenone synthesis was achieved by Pd/NBE‐catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A. |
| doi_str_mv | 10.1002/anie.201813699 |
| format | Article |
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A straightforward method for indenone synthesis was achieved by Pd/NBE‐catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>ISSN: 1521-3773</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201813699</identifier><identifier>PMID: 30600880</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acidic oxides ; acredinone A ; Acylation ; Anhydrides ; Aromatic compounds ; Benzophenones - chemical synthesis ; Benzophenones - chemistry ; Carboxylic acids ; Catalysis ; Chemical reactions ; Chemical synthesis ; Hydrocarbons, Iodinated - chemistry ; Indenes - chemical synthesis ; Indenes - chemistry ; indenone ; Iodides ; Molecular Structure ; Natural products ; Norbornanes - chemistry ; norbornene ; Organic chemistry ; Palladium ; Palladium - chemistry ; pauciflorol F ; Regioselectivity ; Stilbenes - chemical synthesis ; Stilbenes - chemistry ; Substrates</subject><ispartof>Angewandte Chemie International Edition, 2019-02, Vol.58 (7), p.2144-2148</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4499-2b5dac805621dc1eaff1ce2ba2b0fc541612290da2d3d8325403276252018cc63</citedby><cites>FETCH-LOGICAL-c4499-2b5dac805621dc1eaff1ce2ba2b0fc541612290da2d3d8325403276252018cc63</cites><orcidid>0000-0003-1331-6015</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201813699$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201813699$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30600880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Feipeng</creatorcontrib><creatorcontrib>Dong, Zhe</creatorcontrib><creatorcontrib>Wang, Jianchun</creatorcontrib><creatorcontrib>Dong, Guangbin</creatorcontrib><title>Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>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.
A straightforward method for indenone synthesis was achieved by Pd/NBE‐catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A.</description><subject>Acidic oxides</subject><subject>acredinone A</subject><subject>Acylation</subject><subject>Anhydrides</subject><subject>Aromatic compounds</subject><subject>Benzophenones - chemical synthesis</subject><subject>Benzophenones - chemistry</subject><subject>Carboxylic acids</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Hydrocarbons, Iodinated - chemistry</subject><subject>Indenes - chemical synthesis</subject><subject>Indenes - chemistry</subject><subject>indenone</subject><subject>Iodides</subject><subject>Molecular Structure</subject><subject>Natural products</subject><subject>Norbornanes - chemistry</subject><subject>norbornene</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Palladium - chemistry</subject><subject>pauciflorol F</subject><subject>Regioselectivity</subject><subject>Stilbenes - chemical synthesis</subject><subject>Stilbenes - chemistry</subject><subject>Substrates</subject><issn>1433-7851</issn><issn>1521-3773</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkT1vFDEQhi0EIuGgpUSWaGj24o9d7y4F0uqUhJOiEClQW157ljjy2od9G3RUadLnN-aX4NOF46Oh8sjzzKuZ90XoNSVzSgg7Ut7CnBHaUC7a9gk6pBWjBa9r_jTXJedF3VT0AL1I6TrzTUPEc3TAiSAk14fo7kI5p4ydxqPzEPsQPXh4uL1fqLVymx9g8NIb8MEDvtz49RUkm_AQw4gv7bhygLu4cXgZjDWQ3uNF8NqmPQsJhwFfqEnbwYUY3MPt3QlW3uBORzB2q5u_upfo2aBcgleP7wx9OTn-vPhYnH06XS66s0KXZdsWrK-M0g2pBKNGU1DDQDWwXrGeDLoqqaCMtcQoZrhpOKtKwlktWLU1SGvBZ-jDTnc19SMYDX4dlZOraEcVNzIoK__ueHslv4YbKUpGeHZzht49CsTwbYK0lqNNGrKFHsKUJKOC1XWGWUbf_oNehyn6fF6m6orVlWiaTM13lI4hpQjDfhlK5DZhuU1Y7hPOA2_-PGGP_4o0A-0O-G4dbP4jJ7vz5fFv8Z9ltLdf</recordid><startdate>20190211</startdate><enddate>20190211</enddate><creator>Liu, Feipeng</creator><creator>Dong, Zhe</creator><creator>Wang, Jianchun</creator><creator>Dong, Guangbin</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-1331-6015</orcidid></search><sort><creationdate>20190211</creationdate><title>Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A</title><author>Liu, Feipeng ; Dong, Zhe ; Wang, Jianchun ; Dong, Guangbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4499-2b5dac805621dc1eaff1ce2ba2b0fc541612290da2d3d8325403276252018cc63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acidic oxides</topic><topic>acredinone A</topic><topic>Acylation</topic><topic>Anhydrides</topic><topic>Aromatic compounds</topic><topic>Benzophenones - chemical synthesis</topic><topic>Benzophenones - chemistry</topic><topic>Carboxylic acids</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Hydrocarbons, Iodinated - chemistry</topic><topic>Indenes - chemical synthesis</topic><topic>Indenes - chemistry</topic><topic>indenone</topic><topic>Iodides</topic><topic>Molecular Structure</topic><topic>Natural products</topic><topic>Norbornanes - chemistry</topic><topic>norbornene</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Palladium - chemistry</topic><topic>pauciflorol F</topic><topic>Regioselectivity</topic><topic>Stilbenes - chemical synthesis</topic><topic>Stilbenes - chemistry</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Feipeng</creatorcontrib><creatorcontrib>Dong, Zhe</creatorcontrib><creatorcontrib>Wang, Jianchun</creatorcontrib><creatorcontrib>Dong, Guangbin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Feipeng</au><au>Dong, Zhe</au><au>Wang, Jianchun</au><au>Dong, Guangbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-02-11</date><risdate>2019</risdate><volume>58</volume><issue>7</issue><spage>2144</spage><epage>2148</epage><pages>2144-2148</pages><issn>1433-7851</issn><issn>1521-3773</issn><eissn>1521-3773</eissn><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.
A straightforward method for indenone synthesis was achieved by Pd/NBE‐catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30600880</pmid><doi>10.1002/anie.201813699</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-1331-6015</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acidic oxides acredinone A Acylation Anhydrides Aromatic compounds Benzophenones - chemical synthesis Benzophenones - chemistry Carboxylic acids Catalysis Chemical reactions Chemical synthesis Hydrocarbons, Iodinated - chemistry Indenes - chemical synthesis Indenes - chemistry indenone Iodides Molecular Structure Natural products Norbornanes - chemistry norbornene Organic chemistry Palladium Palladium - chemistry pauciflorol F Regioselectivity Stilbenes - chemical synthesis Stilbenes - chemistry Substrates |
| title | Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A |
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