Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products
Bioinspired palladium‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. To demonstrate the practicality of this methodology, the functi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2022-08, Vol.61 (33), p.e202207088-n/a |
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| creator | Li, Quan‐Zhe Hou, Si‐Hua Kang, Jun‐Chen Lian, Peng‐Fei Hao, Yu Chen, Chao Zhou, Jia Ding, Tong‐Mei Zhang, Shu‐Yu |
| description | Bioinspired palladium‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. To demonstrate the practicality of this methodology, the functionalized prolines were used as intermediates for the synthesis of several natural products: lucentamycin A, oxotomaymycin, oxoprothracarcin, and barmumycin.
Bioinspired palladium(II)‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic double bond. Such functionalized prolines were used as intermediates for the total synthesis of several natural products: lucentamycin A, barmumycin, oxotomaymycin, and oxoprothracarcin. |
| doi_str_mv | 10.1002/anie.202207088 |
| format | Article |
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Bioinspired palladium(II)‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic double bond. Such functionalized prolines were used as intermediates for the total synthesis of several natural products: lucentamycin A, barmumycin, oxotomaymycin, and oxoprothracarcin.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202207088</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amino acids ; Bioinspired Synthesis ; Collective Synthesis ; C−H Activation ; Functionalized Prolines ; Intermediates ; Iodides ; Natural products ; Palladium ; Palladium Catalysis ; Proline</subject><ispartof>Angewandte Chemie International Edition, 2022-08, Vol.61 (33), p.e202207088-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3508-7889cbcde8a6755c5fc0eccedd1540047e29f902f4da3b52f33d1bfbcf31e7bb3</citedby><cites>FETCH-LOGICAL-c3508-7889cbcde8a6755c5fc0eccedd1540047e29f902f4da3b52f33d1bfbcf31e7bb3</cites><orcidid>0000-0002-1811-4159</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.202207088$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202207088$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Li, Quan‐Zhe</creatorcontrib><creatorcontrib>Hou, Si‐Hua</creatorcontrib><creatorcontrib>Kang, Jun‐Chen</creatorcontrib><creatorcontrib>Lian, Peng‐Fei</creatorcontrib><creatorcontrib>Hao, Yu</creatorcontrib><creatorcontrib>Chen, Chao</creatorcontrib><creatorcontrib>Zhou, Jia</creatorcontrib><creatorcontrib>Ding, Tong‐Mei</creatorcontrib><creatorcontrib>Zhang, Shu‐Yu</creatorcontrib><title>Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products</title><title>Angewandte Chemie International Edition</title><description>Bioinspired palladium‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. To demonstrate the practicality of this methodology, the functionalized prolines were used as intermediates for the synthesis of several natural products: lucentamycin A, oxotomaymycin, oxoprothracarcin, and barmumycin.
Bioinspired palladium(II)‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic double bond. Such functionalized prolines were used as intermediates for the total synthesis of several natural products: lucentamycin A, barmumycin, oxotomaymycin, and oxoprothracarcin.</description><subject>Amino acids</subject><subject>Bioinspired Synthesis</subject><subject>Collective Synthesis</subject><subject>C−H Activation</subject><subject>Functionalized Prolines</subject><subject>Intermediates</subject><subject>Iodides</subject><subject>Natural products</subject><subject>Palladium</subject><subject>Palladium Catalysis</subject><subject>Proline</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkU1LAzEQhhdRsH5cPQe81ENrPjbd7LEufhREC-p5yWYnmJJuarKr1IsePYo_0V9iSkXBi6eZeXneYYY3SQ4IHhKM6bFsDAwpphRnWIiNpEc4JQOWZWwz9iljg0xwsp3shDCLvBB41EteTowzTVgYDzWaSmtlbbr55-t7IVtpl89RnTStl3NnQXVWelT0w4Idfb59XKCxas2jbI1rkHYetfeACmcjGGVAN8smKsEE5DSaemdNA-hKtp2XdjXXnWrDXrKlpQ2w_113k7uz09viYnB5fT4pxpcDxTgW8XKRq0rVIOQo41xxrTAoBXVNeIpxmgHNdY6pTmvJKk41YzWpdKU0I5BVFdtN-uu9C-8eOghtOTdBQfy3AdeFko4EwSnnIxbRwz_ozHW-iddFKs8FS9OcRGq4ppR3IXjQ5cKbufTLkuBylUe5yqP8ySMa8rXhyVhY_kOX46vJ6a_3C4-Vk0c</recordid><startdate>20220815</startdate><enddate>20220815</enddate><creator>Li, Quan‐Zhe</creator><creator>Hou, Si‐Hua</creator><creator>Kang, Jun‐Chen</creator><creator>Lian, Peng‐Fei</creator><creator>Hao, Yu</creator><creator>Chen, Chao</creator><creator>Zhou, Jia</creator><creator>Ding, Tong‐Mei</creator><creator>Zhang, Shu‐Yu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1811-4159</orcidid></search><sort><creationdate>20220815</creationdate><title>Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products</title><author>Li, Quan‐Zhe ; Hou, Si‐Hua ; Kang, Jun‐Chen ; Lian, Peng‐Fei ; Hao, Yu ; Chen, Chao ; Zhou, Jia ; Ding, Tong‐Mei ; Zhang, Shu‐Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3508-7889cbcde8a6755c5fc0eccedd1540047e29f902f4da3b52f33d1bfbcf31e7bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amino acids</topic><topic>Bioinspired Synthesis</topic><topic>Collective Synthesis</topic><topic>C−H Activation</topic><topic>Functionalized Prolines</topic><topic>Intermediates</topic><topic>Iodides</topic><topic>Natural products</topic><topic>Palladium</topic><topic>Palladium Catalysis</topic><topic>Proline</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Quan‐Zhe</creatorcontrib><creatorcontrib>Hou, Si‐Hua</creatorcontrib><creatorcontrib>Kang, Jun‐Chen</creatorcontrib><creatorcontrib>Lian, Peng‐Fei</creatorcontrib><creatorcontrib>Hao, Yu</creatorcontrib><creatorcontrib>Chen, Chao</creatorcontrib><creatorcontrib>Zhou, Jia</creatorcontrib><creatorcontrib>Ding, Tong‐Mei</creatorcontrib><creatorcontrib>Zhang, Shu‐Yu</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Quan‐Zhe</au><au>Hou, Si‐Hua</au><au>Kang, Jun‐Chen</au><au>Lian, Peng‐Fei</au><au>Hao, Yu</au><au>Chen, Chao</au><au>Zhou, Jia</au><au>Ding, Tong‐Mei</au><au>Zhang, Shu‐Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2022-08-15</date><risdate>2022</risdate><volume>61</volume><issue>33</issue><spage>e202207088</spage><epage>n/a</epage><pages>e202207088-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Bioinspired palladium‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. To demonstrate the practicality of this methodology, the functionalized prolines were used as intermediates for the synthesis of several natural products: lucentamycin A, oxotomaymycin, oxoprothracarcin, and barmumycin.
Bioinspired palladium(II)‐catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic double bond. Such functionalized prolines were used as intermediates for the total synthesis of several natural products: lucentamycin A, barmumycin, oxotomaymycin, and oxoprothracarcin.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.202207088</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-1811-4159</orcidid></addata></record> |
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| subjects | Amino acids Bioinspired Synthesis Collective Synthesis C−H Activation Functionalized Prolines Intermediates Iodides Natural products Palladium Palladium Catalysis Proline |
| title | Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products |
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