Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications
We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an N -bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy an...
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| Veröffentlicht in: | Science China. Chemistry 2023-11, Vol.66 (11), p.3136-3140 |
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| container_end_page | 3140 |
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| container_issue | 11 |
| container_start_page | 3136 |
| container_title | Science China. Chemistry |
| container_volume | 66 |
| creator | Jia, Shihu Bai, Miao Zhou, Siwei Sheng, Ruiqing Cheng, Hong-Gang Zhou, Qianghui |
| description | We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an
N
-bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy and good scalability. Based on this new method, we have accomplished the concise total synthesis of (±)-cularine, formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A, demonstrating the wide synthetic potential of this method. |
| doi_str_mv | 10.1007/s11426-022-1526-7 |
| format | Article |
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N
-bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy and good scalability. Based on this new method, we have accomplished the concise total synthesis of (±)-cularine, formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A, demonstrating the wide synthetic potential of this method.</description><identifier>ISSN: 1674-7291</identifier><identifier>EISSN: 1869-1870</identifier><identifier>DOI: 10.1007/s11426-022-1526-7</identifier><language>eng</language><publisher>Beijing: Science China Press</publisher><subject>Alkynes ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Communications ; Ligands ; Substrates ; Synthesis</subject><ispartof>Science China. Chemistry, 2023-11, Vol.66 (11), p.3136-3140</ispartof><rights>Science China Press 2023</rights><rights>Science China Press 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-d810eb5f733dbbdba48f587b46209173a1387003215c35d93ff9051febf1c0a63</citedby><cites>FETCH-LOGICAL-c316t-d810eb5f733dbbdba48f587b46209173a1387003215c35d93ff9051febf1c0a63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11426-022-1526-7$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2918646194?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,21387,21388,21389,21390,23255,27923,27924,33529,33702,33743,34004,34313,41487,42556,43658,43786,43804,43952,44066,51318,64384,64388,72240</link.rule.ids></links><search><creatorcontrib>Jia, Shihu</creatorcontrib><creatorcontrib>Bai, Miao</creatorcontrib><creatorcontrib>Zhou, Siwei</creatorcontrib><creatorcontrib>Sheng, Ruiqing</creatorcontrib><creatorcontrib>Cheng, Hong-Gang</creatorcontrib><creatorcontrib>Zhou, Qianghui</creatorcontrib><title>Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications</title><title>Science China. Chemistry</title><addtitle>Sci. China Chem</addtitle><description>We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an
N
-bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy and good scalability. Based on this new method, we have accomplished the concise total synthesis of (±)-cularine, formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A, demonstrating the wide synthetic potential of this method.</description><subject>Alkynes</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Communications</subject><subject>Ligands</subject><subject>Substrates</subject><subject>Synthesis</subject><issn>1674-7291</issn><issn>1869-1870</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp1kM9KxDAQxosoKOoDeAt4jmaatmmPuvgPFkXUc0iTiUaz6Zp0hfoOvrNZV_DkXGbg-74Z5lcUR8BOgDFxmgCqsqGsLCnUeRBbxR60TUehFWw7z42oqCg72C0OU3pluThnpaj3iq_7ldNvRKWEi95PZLAEqPJvk3cGw-TpiGNUL5OJg0vD-8qFwbuAiXw4RRSZqRG9V8GRiEqPbgint-cPdIHGZcUQPWnvPtVaIAnfVxg0EhUMSVMYX3B0mqjl0jv9Y0kHxY5VPuHhb98vni4vHmfXdH53dTM7m1PNoRmpaYFhX1vBuel706uqtXUr-qopWQeCK-D5ccZLqDWvTcet7VgNFnsLmqmG7xfHm73LmH_CNMrXYRVDPikzpbapGuiq7IKNS8chpYhWLqNbqDhJYHINXm7AywxersFLkTPlJpOyNzxj_Nv8f-gbHbSIvA</recordid><startdate>20231101</startdate><enddate>20231101</enddate><creator>Jia, Shihu</creator><creator>Bai, Miao</creator><creator>Zhou, Siwei</creator><creator>Sheng, Ruiqing</creator><creator>Cheng, Hong-Gang</creator><creator>Zhou, Qianghui</creator><general>Science China Press</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FG</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>M2P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>20231101</creationdate><title>Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications</title><author>Jia, Shihu ; Bai, Miao ; Zhou, Siwei ; Sheng, Ruiqing ; Cheng, Hong-Gang ; Zhou, Qianghui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-d810eb5f733dbbdba48f587b46209173a1387003215c35d93ff9051febf1c0a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkynes</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Communications</topic><topic>Ligands</topic><topic>Substrates</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jia, Shihu</creatorcontrib><creatorcontrib>Bai, Miao</creatorcontrib><creatorcontrib>Zhou, Siwei</creatorcontrib><creatorcontrib>Sheng, Ruiqing</creatorcontrib><creatorcontrib>Cheng, Hong-Gang</creatorcontrib><creatorcontrib>Zhou, Qianghui</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Science China. Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jia, Shihu</au><au>Bai, Miao</au><au>Zhou, Siwei</au><au>Sheng, Ruiqing</au><au>Cheng, Hong-Gang</au><au>Zhou, Qianghui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications</atitle><jtitle>Science China. Chemistry</jtitle><stitle>Sci. China Chem</stitle><date>2023-11-01</date><risdate>2023</risdate><volume>66</volume><issue>11</issue><spage>3136</spage><epage>3140</epage><pages>3136-3140</pages><issn>1674-7291</issn><eissn>1869-1870</eissn><abstract>We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an
N
-bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy and good scalability. Based on this new method, we have accomplished the concise total synthesis of (±)-cularine, formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A, demonstrating the wide synthetic potential of this method.</abstract><cop>Beijing</cop><pub>Science China Press</pub><doi>10.1007/s11426-022-1526-7</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkynes Chemistry Chemistry and Materials Science Chemistry/Food Science Communications Ligands Substrates Synthesis |
| title | Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications |
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