A Total Synthesis of (±)‐Ceratopicanol via Palladium Catalyzed Reductive Cyclization
An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to for...
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| Veröffentlicht in: | European journal of organic chemistry 2020-08, Vol.2020 (31), p.4931-4936 |
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| container_issue | 31 |
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| container_title | European journal of organic chemistry |
| container_volume | 2020 |
| creator | Kim, Rira Lee, Sanghyeon Lee, Jaeyeon Lee, Hee‐Yoon |
| description | An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.
An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions. |
| doi_str_mv | 10.1002/ejoc.202000769 |
| format | Article |
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An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202000769</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemical reactions ; Chemical synthesis ; Cyclization ; Cycloaddition ; Free radicals ; Palladium ; Pd catalysis ; Total synthesis ; Triquinane</subject><ispartof>European journal of organic chemistry, 2020-08, Vol.2020 (31), p.4931-4936</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2729-5b37297a5c0c370b163beb44c0db42684feaa2b5b1c8b54d9c0fae2426c11ac83</cites><orcidid>0000-0002-3558-2894</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%2Fejoc.202000769$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202000769$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Kim, Rira</creatorcontrib><creatorcontrib>Lee, Sanghyeon</creatorcontrib><creatorcontrib>Lee, Jaeyeon</creatorcontrib><creatorcontrib>Lee, Hee‐Yoon</creatorcontrib><title>A Total Synthesis of (±)‐Ceratopicanol via Palladium Catalyzed Reductive Cyclization</title><title>European journal of organic chemistry</title><description>An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.
An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.</description><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Cyclization</subject><subject>Cycloaddition</subject><subject>Free radicals</subject><subject>Palladium</subject><subject>Pd catalysis</subject><subject>Total synthesis</subject><subject>Triquinane</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkMtKAzEUhoMoWKtb1wE3upia28w0yzLUG4WKVnQXkkwGU6aTOpmpTFc-gq_iK_goPokpFV26-g-c7zsHfgCOMRpghMi5mTs9IIgghNKE74AeRpxHKOFoN8yMsghz-rQPDryfB4YnCe6BxxGcuUaW8L6rmmfjrYeugKefH2dfb--ZqWXjllbLypVwZSW8lWUpc9suYCaD1a1NDu9M3urGrgzMOl3atWysqw7BXiFLb45-sg8eLsaz7CqaTC-vs9Ek0iQlPIoVDZHKWCNNU6RwQpVRjGmUK0aSISuMlETFCuuhilnONSqkIWGlMZZ6SPvgZHt3WbuX1vhGzF1bV-GlIIzGKcYxTwI12FK6dt7XphDL2i5k3QmMxKY8sSlP_JYXBL4VXm1pun9oMb6ZZn_uN_HGdTQ</recordid><startdate>20200823</startdate><enddate>20200823</enddate><creator>Kim, Rira</creator><creator>Lee, Sanghyeon</creator><creator>Lee, Jaeyeon</creator><creator>Lee, Hee‐Yoon</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3558-2894</orcidid></search><sort><creationdate>20200823</creationdate><title>A Total Synthesis of (±)‐Ceratopicanol via Palladium Catalyzed Reductive Cyclization</title><author>Kim, Rira ; Lee, Sanghyeon ; Lee, Jaeyeon ; Lee, Hee‐Yoon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2729-5b37297a5c0c370b163beb44c0db42684feaa2b5b1c8b54d9c0fae2426c11ac83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Cyclization</topic><topic>Cycloaddition</topic><topic>Free radicals</topic><topic>Palladium</topic><topic>Pd catalysis</topic><topic>Total synthesis</topic><topic>Triquinane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Rira</creatorcontrib><creatorcontrib>Lee, Sanghyeon</creatorcontrib><creatorcontrib>Lee, Jaeyeon</creatorcontrib><creatorcontrib>Lee, Hee‐Yoon</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Rira</au><au>Lee, Sanghyeon</au><au>Lee, Jaeyeon</au><au>Lee, Hee‐Yoon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Total Synthesis of (±)‐Ceratopicanol via Palladium Catalyzed Reductive Cyclization</atitle><jtitle>European journal of organic chemistry</jtitle><date>2020-08-23</date><risdate>2020</risdate><volume>2020</volume><issue>31</issue><spage>4931</spage><epage>4936</epage><pages>4931-4936</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.
An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202000769</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3558-2894</orcidid></addata></record> |
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| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Chemical reactions Chemical synthesis Cyclization Cycloaddition Free radicals Palladium Pd catalysis Total synthesis Triquinane |
| title | A Total Synthesis of (±)‐Ceratopicanol via Palladium Catalyzed Reductive Cyclization |
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