A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes
A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to...
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Veröffentlicht in: | Organic & biomolecular chemistry 2018-12, Vol.16 (47), p.9147-9151 |
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container_title | Organic & biomolecular chemistry |
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creator | Guo, Jia Peng, Xiaoshi Wang, Xiaoyu Xie, Fukai Zhang, Xinhang Liang, Guoduan Sun, Zenghui Liu, Yongxiang Cheng, Maosheng Liu, Yang |
description | A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin. |
doi_str_mv | 10.1039/c8ob02582g |
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The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c8ob02582g</identifier><identifier>PMID: 30465587</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Crystallography ; Gold ; Isomerization ; Labeling ; Oxidation ; Oxygen ; Reaction mechanisms ; Substrates</subject><ispartof>Organic & biomolecular chemistry, 2018-12, Vol.16 (47), p.9147-9151</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-f0150a1f728becd4ed1deec0bc1b9965cd3c4f5644613b41e367e40ce57ba6173</citedby><cites>FETCH-LOGICAL-c315t-f0150a1f728becd4ed1deec0bc1b9965cd3c4f5644613b41e367e40ce57ba6173</cites><orcidid>0000-0003-0364-0137 ; 0000-0002-9284-1944</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30465587$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Jia</creatorcontrib><creatorcontrib>Peng, Xiaoshi</creatorcontrib><creatorcontrib>Wang, Xiaoyu</creatorcontrib><creatorcontrib>Xie, Fukai</creatorcontrib><creatorcontrib>Zhang, Xinhang</creatorcontrib><creatorcontrib>Liang, Guoduan</creatorcontrib><creatorcontrib>Sun, Zenghui</creatorcontrib><creatorcontrib>Liu, Yongxiang</creatorcontrib><creatorcontrib>Cheng, Maosheng</creatorcontrib><creatorcontrib>Liu, Yang</creatorcontrib><title>A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.</description><subject>Aromatic compounds</subject><subject>Crystallography</subject><subject>Gold</subject><subject>Isomerization</subject><subject>Labeling</subject><subject>Oxidation</subject><subject>Oxygen</subject><subject>Reaction mechanisms</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LwzAYgIMobk4v_gAJeBGxLmmSpj3OoVMY7KLnkiZvR2fbzKQDu19v3OYOnt4PHh7eD4SuKXmkhGVjndqCxCKNlydoSLmUEREsOz3mMRmgC-9XhNBMJvwcDRjhiRCpHKLPCV7a2kRadarut2Cw7nVtK28bcNVWdZVtxwqcLSqN7Xdldh2sldfKAPadUx0se1xah-NIub7GVWugtS14XDrbYPogImj7UF-is1LVHq4OcYQ-Xp7fp6_RfDF7m07mkWZUdFFJqCCKljJOC9CGg6EGQJNC0yLLEqEN07wUCecJZQWnwBIJnGgQslAJlWyE7vbetbNfG_Bd3lReQ12rFuzG53HwC0akoAG9_Yeu7Ma1YbodRYOaZ4G631PaWe8dlPnaVU1YNqck_31BPk0XT7sXzAJ8c1BuigbMEf27OfsBD1mBzQ</recordid><startdate>20181205</startdate><enddate>20181205</enddate><creator>Guo, Jia</creator><creator>Peng, Xiaoshi</creator><creator>Wang, Xiaoyu</creator><creator>Xie, Fukai</creator><creator>Zhang, Xinhang</creator><creator>Liang, Guoduan</creator><creator>Sun, Zenghui</creator><creator>Liu, Yongxiang</creator><creator>Cheng, Maosheng</creator><creator>Liu, Yang</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0364-0137</orcidid><orcidid>https://orcid.org/0000-0002-9284-1944</orcidid></search><sort><creationdate>20181205</creationdate><title>A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes</title><author>Guo, Jia ; Peng, Xiaoshi ; Wang, Xiaoyu ; Xie, Fukai ; Zhang, Xinhang ; Liang, Guoduan ; Sun, Zenghui ; Liu, Yongxiang ; Cheng, Maosheng ; Liu, Yang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-f0150a1f728becd4ed1deec0bc1b9965cd3c4f5644613b41e367e40ce57ba6173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Crystallography</topic><topic>Gold</topic><topic>Isomerization</topic><topic>Labeling</topic><topic>Oxidation</topic><topic>Oxygen</topic><topic>Reaction mechanisms</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Jia</creatorcontrib><creatorcontrib>Peng, Xiaoshi</creatorcontrib><creatorcontrib>Wang, Xiaoyu</creatorcontrib><creatorcontrib>Xie, Fukai</creatorcontrib><creatorcontrib>Zhang, Xinhang</creatorcontrib><creatorcontrib>Liang, Guoduan</creatorcontrib><creatorcontrib>Sun, Zenghui</creatorcontrib><creatorcontrib>Liu, Yongxiang</creatorcontrib><creatorcontrib>Cheng, Maosheng</creatorcontrib><creatorcontrib>Liu, Yang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guo, Jia</au><au>Peng, Xiaoshi</au><au>Wang, Xiaoyu</au><au>Xie, Fukai</au><au>Zhang, Xinhang</au><au>Liang, Guoduan</au><au>Sun, Zenghui</au><au>Liu, Yongxiang</au><au>Cheng, Maosheng</au><au>Liu, Yang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2018-12-05</date><risdate>2018</risdate><volume>16</volume><issue>47</issue><spage>9147</spage><epage>9151</epage><pages>9147-9151</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. 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source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
subjects | Aromatic compounds Crystallography Gold Isomerization Labeling Oxidation Oxygen Reaction mechanisms Substrates |
title | A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes |
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