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A Diels-Alder Approach to Anthrapyran Antibiotics
Abstract A new entry to the synthesis of anthrapyran antibiotics has been accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model. The key step features a Diels-Alder reaction between a substituted 5-vinyl-3,4-dihydro-2H-pyran and naphthoquinone as the dienophile. The resul...
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| Published in: | Synlett 2012-03, Vol.23 (5), p.768-772 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c341t-85dfd8e5d6e2e57a3412f301df87a67b7e6acef695424db1c46d2eaa750d4d393 |
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| container_end_page | 772 |
| container_issue | 5 |
| container_start_page | 768 |
| container_title | Synlett |
| container_volume | 23 |
| creator | Foulgoc, Laura Sissouma, Drissa Evain, Michel Collet, Sylvain Guingant, André |
| description | Abstract
A new entry to the synthesis of anthrapyran antibiotics has been
accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model.
The key step features a Diels-Alder reaction between a
substituted 5-vinyl-3,4-dihydro-2H-pyran
and naphthoquinone as the dienophile. The resulting tetracyclic
adduct is then processed towards the targeted trione in a few steps. |
| doi_str_mv | 10.1055/s-0031-1290529 |
| format | article |
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A new entry to the synthesis of anthrapyran antibiotics has been
accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model.
The key step features a Diels-Alder reaction between a
substituted 5-vinyl-3,4-dihydro-2H-pyran
and naphthoquinone as the dienophile. The resulting tetracyclic
adduct is then processed towards the targeted trione in a few steps.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-0031-1290529</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Biological and medical sciences ; Chemistry ; Condensed benzenic and aromatic compounds ; Condensed Matter ; Exact sciences and technology ; General aspects ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; letter ; Materials Science ; Medical sciences ; Noncondensed benzenic compounds ; Organic chemistry ; Pharmacology. Drug treatments ; Physics ; Preparations and properties</subject><ispartof>Synlett, 2012-03, Vol.23 (5), p.768-772</ispartof><rights>Georg Thieme Verlag Stuttgart ˙ New York</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c341t-85dfd8e5d6e2e57a3412f301df87a67b7e6acef695424db1c46d2eaa750d4d393</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0031-1290529.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0031-1290529$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>230,314,780,784,885,3017,3018,27924,27925,54559,54560</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25626246$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00864705$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Foulgoc, Laura</creatorcontrib><creatorcontrib>Sissouma, Drissa</creatorcontrib><creatorcontrib>Evain, Michel</creatorcontrib><creatorcontrib>Collet, Sylvain</creatorcontrib><creatorcontrib>Guingant, André</creatorcontrib><title>A Diels-Alder Approach to Anthrapyran Antibiotics</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract
A new entry to the synthesis of anthrapyran antibiotics has been
accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model.
The key step features a Diels-Alder reaction between a
substituted 5-vinyl-3,4-dihydro-2H-pyran
and naphthoquinone as the dienophile. The resulting tetracyclic
adduct is then processed towards the targeted trione in a few steps.</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Condensed Matter</subject><subject>Exact sciences and technology</subject><subject>General aspects</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>letter</subject><subject>Materials Science</subject><subject>Medical sciences</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Physics</subject><subject>Preparations and properties</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp1kEtLw0AUhQdRsFa3rrNx4WL0zjOZZaiPCgU3uh6m8yBT0ibMRKH_3oSU7lzdy-E7B85B6J7AEwEhnjMGYAQTqkBQdYEWhLMSU1DyEi1AMYkFJfwa3eS8AyC8UrBApC5eom8zrlvnU1H3feqMbYqhK-rD0CTTH5M5TH_cxm6INt-iq2Da7O9Od4m-316_Vmu8-Xz_WNUbbBknA66EC67ywklPvSjNKNLAgLhQlUaW29JLY32QSnDK3ZZYLh31xpQCHHdMsSV6nHMb0-o-xb1JR92ZqNf1Rk8aQCV5CeKXjOzTzNrU5Zx8OBsI6GkcnfU0jj6NMxoeZkNvsjVtGDvamM8uKiSVlMuRwzM3NNHvvd51P-kwtv4v9w8_xHBN</recordid><startdate>20120301</startdate><enddate>20120301</enddate><creator>Foulgoc, Laura</creator><creator>Sissouma, Drissa</creator><creator>Evain, Michel</creator><creator>Collet, Sylvain</creator><creator>Guingant, André</creator><general>Thieme</general><general>Georg Thieme Verlag</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope></search><sort><creationdate>20120301</creationdate><title>A Diels-Alder Approach to Anthrapyran Antibiotics</title><author>Foulgoc, Laura ; Sissouma, Drissa ; Evain, Michel ; Collet, Sylvain ; Guingant, André</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c341t-85dfd8e5d6e2e57a3412f301df87a67b7e6acef695424db1c46d2eaa750d4d393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Condensed Matter</topic><topic>Exact sciences and technology</topic><topic>General aspects</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>letter</topic><topic>Materials Science</topic><topic>Medical sciences</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Physics</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Foulgoc, Laura</creatorcontrib><creatorcontrib>Sissouma, Drissa</creatorcontrib><creatorcontrib>Evain, Michel</creatorcontrib><creatorcontrib>Collet, Sylvain</creatorcontrib><creatorcontrib>Guingant, André</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Foulgoc, Laura</au><au>Sissouma, Drissa</au><au>Evain, Michel</au><au>Collet, Sylvain</au><au>Guingant, André</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Diels-Alder Approach to Anthrapyran Antibiotics</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2012-03-01</date><risdate>2012</risdate><volume>23</volume><issue>5</issue><spage>768</spage><epage>772</epage><pages>768-772</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract
A new entry to the synthesis of anthrapyran antibiotics has been
accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model.
The key step features a Diels-Alder reaction between a
substituted 5-vinyl-3,4-dihydro-2H-pyran
and naphthoquinone as the dienophile. The resulting tetracyclic
adduct is then processed towards the targeted trione in a few steps.</abstract><cop>Stuttgart</cop><pub>Thieme</pub><doi>10.1055/s-0031-1290529</doi><tpages>5</tpages></addata></record> |
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| ispartof | Synlett, 2012-03, Vol.23 (5), p.768-772 |
| issn | 0936-5214 1437-2096 |
| language | eng |
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| source | Thieme - Connect here FIRST to enable access |
| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Chemistry Condensed benzenic and aromatic compounds Condensed Matter Exact sciences and technology General aspects Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives letter Materials Science Medical sciences Noncondensed benzenic compounds Organic chemistry Pharmacology. Drug treatments Physics Preparations and properties |
| title | A Diels-Alder Approach to Anthrapyran Antibiotics |
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