Zeolite‐Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal‐Doped Zeolite‐Catalyzed Steps
Similarly to polymer‐supported assisted synthesis (PSAS), organic synthesis could be envisaged being performed by using zeolites, native or metal‐doped, as heterogeneous catalysts. To illustrate this unprecedented Zeolite‐Based Organic Synthesis (ZeoBOS), the total synthesis of acortatarin A was ach...
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creator | Wimmer, Eric Borghèse, Sophie Blanc, Aurélien Bénéteau, Valérie Pale, Patrick |
description | Similarly to polymer‐supported assisted synthesis (PSAS), organic synthesis could be envisaged being performed by using zeolites, native or metal‐doped, as heterogeneous catalysts. To illustrate this unprecedented Zeolite‐Based Organic Synthesis (ZeoBOS), the total synthesis of acortatarin A was achieved through a novel strategy and using five out of eleven synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts. Notably, the formation of an yne‐pyrrole intermediate with a copper‐doped zeolite and the spiroketalization of an alkyne diol with a silver‐doped zeolite have been developed as key steps of the synthesis.
A new concept, that is, Zeolite‐Based Organic Synthesis (ZeoBOS), is described for the efficient access to structurally complex and functionalized molecules and illustrated with the total synthesis of acortatarin A, a unique antioxidant natural product. The synthesis was achieved through a novel strategy, based on several synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts. |
doi_str_mv | 10.1002/chem.201605048 |
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A new concept, that is, Zeolite‐Based Organic Synthesis (ZeoBOS), is described for the efficient access to structurally complex and functionalized molecules and illustrated with the total synthesis of acortatarin A, a unique antioxidant natural product. The synthesis was achieved through a novel strategy, based on several synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201605048</identifier><identifier>PMID: 28090685</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Catalysis ; Catalysts ; Chemical bonds ; Chemistry ; copper ; Diols ; doped-zeolite ; silver ; spiroketalization ; Strategy ; Synthesis ; Synthesis (chemistry) ; ynamide formation ; Zeolites</subject><ispartof>Chemistry : a European journal, 2017-01, Vol.23 (7), p.1484-1489</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4438-1a0bd3b966571c601bf2afb499bbe9bab66265e6baa441ca026f12ff35cf05333</citedby><cites>FETCH-LOGICAL-c4438-1a0bd3b966571c601bf2afb499bbe9bab66265e6baa441ca026f12ff35cf05333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201605048$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201605048$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28090685$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wimmer, Eric</creatorcontrib><creatorcontrib>Borghèse, Sophie</creatorcontrib><creatorcontrib>Blanc, Aurélien</creatorcontrib><creatorcontrib>Bénéteau, Valérie</creatorcontrib><creatorcontrib>Pale, Patrick</creatorcontrib><title>Zeolite‐Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal‐Doped Zeolite‐Catalyzed Steps</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Similarly to polymer‐supported assisted synthesis (PSAS), organic synthesis could be envisaged being performed by using zeolites, native or metal‐doped, as heterogeneous catalysts. To illustrate this unprecedented Zeolite‐Based Organic Synthesis (ZeoBOS), the total synthesis of acortatarin A was achieved through a novel strategy and using five out of eleven synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts. Notably, the formation of an yne‐pyrrole intermediate with a copper‐doped zeolite and the spiroketalization of an alkyne diol with a silver‐doped zeolite have been developed as key steps of the synthesis.
A new concept, that is, Zeolite‐Based Organic Synthesis (ZeoBOS), is described for the efficient access to structurally complex and functionalized molecules and illustrated with the total synthesis of acortatarin A, a unique antioxidant natural product. The synthesis was achieved through a novel strategy, based on several synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts.</description><subject>Alkynes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>copper</subject><subject>Diols</subject><subject>doped-zeolite</subject><subject>silver</subject><subject>spiroketalization</subject><subject>Strategy</subject><subject>Synthesis</subject><subject>Synthesis (chemistry)</subject><subject>ynamide formation</subject><subject>Zeolites</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkc9uEzEQhy0EoqFw5YgscSmHDeO_WXNLQ0uRWnJIuXBZ2Y5NXW3WwXZA4cQTIJ6RJ8FRSou4wGkkzzffyPND6CmBMQGgL-2VW40pEAkCeHsPjYigpGETKe6jESg-aaRg6gA9yvkaAJRk7CE6oC0okK0Yoe8fXOxDcT-__TjW2S3xPH3UQ7B4sR3Klcsh46OKHM8XL3D0eGpjKrroFAY8fYVPQ8oFX8ai-z8G9qI44He6hM8O62GJL1xl6pLXcV17d0tnVdZvv9a3RXHr_Bg98LrP7slNPUTvT08uZ2fN-fzN29n0vLGcs7YhGsySGSWlmBArgRhPtTdcKWOcMtpISaVw0mjNObEaqPSEes-E9SAYY4foaO9dp_hp43LpViFb1_d6cHGTO9K2vN53wsV_oLLeXLQKKvr8L_Q6btJQP7KjGAUmCK_UeE_ZFHNOznfrFFY6bTsC3S7UbhdqdxtqHXh2o92YlVve4r9TrIDaA19C77b_0HWzs5OLO_kvtYuwcw</recordid><startdate>20170131</startdate><enddate>20170131</enddate><creator>Wimmer, Eric</creator><creator>Borghèse, Sophie</creator><creator>Blanc, Aurélien</creator><creator>Bénéteau, Valérie</creator><creator>Pale, Patrick</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20170131</creationdate><title>Zeolite‐Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal‐Doped Zeolite‐Catalyzed Steps</title><author>Wimmer, Eric ; Borghèse, Sophie ; Blanc, Aurélien ; Bénéteau, Valérie ; Pale, Patrick</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4438-1a0bd3b966571c601bf2afb499bbe9bab66265e6baa441ca026f12ff35cf05333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>copper</topic><topic>Diols</topic><topic>doped-zeolite</topic><topic>silver</topic><topic>spiroketalization</topic><topic>Strategy</topic><topic>Synthesis</topic><topic>Synthesis (chemistry)</topic><topic>ynamide formation</topic><topic>Zeolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wimmer, Eric</creatorcontrib><creatorcontrib>Borghèse, Sophie</creatorcontrib><creatorcontrib>Blanc, Aurélien</creatorcontrib><creatorcontrib>Bénéteau, Valérie</creatorcontrib><creatorcontrib>Pale, Patrick</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wimmer, Eric</au><au>Borghèse, Sophie</au><au>Blanc, Aurélien</au><au>Bénéteau, Valérie</au><au>Pale, Patrick</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Zeolite‐Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal‐Doped Zeolite‐Catalyzed Steps</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-01-31</date><risdate>2017</risdate><volume>23</volume><issue>7</issue><spage>1484</spage><epage>1489</epage><pages>1484-1489</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Similarly to polymer‐supported assisted synthesis (PSAS), organic synthesis could be envisaged being performed by using zeolites, native or metal‐doped, as heterogeneous catalysts. To illustrate this unprecedented Zeolite‐Based Organic Synthesis (ZeoBOS), the total synthesis of acortatarin A was achieved through a novel strategy and using five out of eleven synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts. Notably, the formation of an yne‐pyrrole intermediate with a copper‐doped zeolite and the spiroketalization of an alkyne diol with a silver‐doped zeolite have been developed as key steps of the synthesis.
A new concept, that is, Zeolite‐Based Organic Synthesis (ZeoBOS), is described for the efficient access to structurally complex and functionalized molecules and illustrated with the total synthesis of acortatarin A, a unique antioxidant natural product. The synthesis was achieved through a novel strategy, based on several synthetic steps catalyzed by H‐ or metal‐doped zeolites as catalysts.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28090685</pmid><doi>10.1002/chem.201605048</doi><tpages>6</tpages></addata></record> |
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subjects | Alkynes Catalysis Catalysts Chemical bonds Chemistry copper Diols doped-zeolite silver spiroketalization Strategy Synthesis Synthesis (chemistry) ynamide formation Zeolites |
title | Zeolite‐Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal‐Doped Zeolite‐Catalyzed Steps |
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