Assembly of Terpenoid Cores by a Simple, Tunable Strategy
Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scal...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-12, Vol.55 (51), p.15792-15796 |
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| container_issue | 51 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Lahtigui, Ouidad Emmetiere, Fabien Zhang, Wei Jirmo, Liban Toledo-Roy, Samira Hershberger, John C. Macho, Jocelyn M. Grenning, Alexander J. |
| description | Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
How to Cope with a synthesis problem: Total synthesis of oxygenated, polycyclic terpenes is widely studied, although synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Here presented is a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles. |
| doi_str_mv | 10.1002/anie.201608863 |
| format | Article |
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How to Cope with a synthesis problem: Total synthesis of oxygenated, polycyclic terpenes is widely studied, although synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Here presented is a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201608863</identifier><identifier>PMID: 27860109</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>3] Cope rearrangement ; [3,3] Cope rearrangement ; allylic alkylation ; deconjugative alkylation ; Knoevenagel adducts ; terpene synthesis</subject><ispartof>Angewandte Chemie International Edition, 2016-12, Vol.55 (51), p.15792-15796</ispartof><rights>2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5143-e50e9f40d7169864a15c7aa69804f01f114b6c19dc569cf5dbba6692d7c32a2c3</citedby><cites>FETCH-LOGICAL-c5143-e50e9f40d7169864a15c7aa69804f01f114b6c19dc569cf5dbba6692d7c32a2c3</cites><orcidid>0000-0002-8182-9464</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.201608863$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201608863$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27860109$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lahtigui, Ouidad</creatorcontrib><creatorcontrib>Emmetiere, Fabien</creatorcontrib><creatorcontrib>Zhang, Wei</creatorcontrib><creatorcontrib>Jirmo, Liban</creatorcontrib><creatorcontrib>Toledo-Roy, Samira</creatorcontrib><creatorcontrib>Hershberger, John C.</creatorcontrib><creatorcontrib>Macho, Jocelyn M.</creatorcontrib><creatorcontrib>Grenning, Alexander J.</creatorcontrib><title>Assembly of Terpenoid Cores by a Simple, Tunable Strategy</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
How to Cope with a synthesis problem: Total synthesis of oxygenated, polycyclic terpenes is widely studied, although synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Here presented is a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles.</description><subject>3] Cope rearrangement</subject><subject>[3,3] Cope rearrangement</subject><subject>allylic alkylation</subject><subject>deconjugative alkylation</subject><subject>Knoevenagel adducts</subject><subject>terpene synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkL1v2zAUxImgQeKkXTMWArp0iBw-UiKp0TAcJ2ngDnZbIAtBUU-FXH24pIVE_31o2DWKLJneDb-7dzhCroCOgVJ2Y9oKx4yCoEoJfkJGkDKIuZT8Q9AJ57FUKZyTC-_XgVeKijNyzqQSFGg2ItnEe2zyeoi6Mlqh22DbVUU07Rz6KB8iEy2rZlPjdbTqW5PXGC23zmzx9_CRnJam9vjpcC_Jj9vZanoXP36f308nj7FNw_8YU4pZmdBCgsiUSAykVhoTNE1KCiVAkgsLWWFTkdkyLfLcCJGxQlrODLP8knzd525c97dHv9VN5S3WtWmx670GlYCiTAAL6Jc36LrrXRva7SilAJSQgRrvKes67x2WeuOqxrhBA9W7UfVuVH0cNRg-H2L7vMHiiP9bMQDZHniuahzeidOTxf3s__B47638Fl-OXuP-6NBVpvrXYq4XD5Q_rX5-01P-Cnjmj_8</recordid><startdate>20161219</startdate><enddate>20161219</enddate><creator>Lahtigui, Ouidad</creator><creator>Emmetiere, Fabien</creator><creator>Zhang, Wei</creator><creator>Jirmo, Liban</creator><creator>Toledo-Roy, Samira</creator><creator>Hershberger, John C.</creator><creator>Macho, Jocelyn M.</creator><creator>Grenning, Alexander J.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8182-9464</orcidid></search><sort><creationdate>20161219</creationdate><title>Assembly of Terpenoid Cores by a Simple, Tunable Strategy</title><author>Lahtigui, Ouidad ; Emmetiere, Fabien ; Zhang, Wei ; Jirmo, Liban ; Toledo-Roy, Samira ; Hershberger, John C. ; Macho, Jocelyn M. ; Grenning, Alexander J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5143-e50e9f40d7169864a15c7aa69804f01f114b6c19dc569cf5dbba6692d7c32a2c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>3] Cope rearrangement</topic><topic>[3,3] Cope rearrangement</topic><topic>allylic alkylation</topic><topic>deconjugative alkylation</topic><topic>Knoevenagel adducts</topic><topic>terpene synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lahtigui, Ouidad</creatorcontrib><creatorcontrib>Emmetiere, Fabien</creatorcontrib><creatorcontrib>Zhang, Wei</creatorcontrib><creatorcontrib>Jirmo, Liban</creatorcontrib><creatorcontrib>Toledo-Roy, Samira</creatorcontrib><creatorcontrib>Hershberger, John C.</creatorcontrib><creatorcontrib>Macho, Jocelyn M.</creatorcontrib><creatorcontrib>Grenning, Alexander J.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><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>Lahtigui, Ouidad</au><au>Emmetiere, Fabien</au><au>Zhang, Wei</au><au>Jirmo, Liban</au><au>Toledo-Roy, Samira</au><au>Hershberger, John C.</au><au>Macho, Jocelyn M.</au><au>Grenning, Alexander J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Assembly of Terpenoid Cores by a Simple, Tunable Strategy</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-12-19</date><risdate>2016</risdate><volume>55</volume><issue>51</issue><spage>15792</spage><epage>15796</epage><pages>15792-15796</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
How to Cope with a synthesis problem: Total synthesis of oxygenated, polycyclic terpenes is widely studied, although synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Here presented is a simple, scalable, and tunable synthetic strategy to assemble terpenoid‐like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27860109</pmid><doi>10.1002/anie.201608863</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-8182-9464</orcidid></addata></record> |
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| subjects | 3] Cope rearrangement [3,3] Cope rearrangement allylic alkylation deconjugative alkylation Knoevenagel adducts terpene synthesis |
| title | Assembly of Terpenoid Cores by a Simple, Tunable Strategy |
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