Direct and Short Construction of the ACDE Ring System of Daphenylline
Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthes...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2015-02, Vol.10 (2), p.377-382 |
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| creator | Wang, Wei Li, Guo-Ping Wang, Shao-Feng Shi, Zi-Fa Cao, Xiao-Ping |
| description | Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization and an intramolecular Friedel–Crafts acylation.
Ring ring, ACDE: A direct and short construction of the ACDE ring system of daphenylline has been accomplished from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization, and an intramolecular Friedel–Crafts acylation. |
| doi_str_mv | 10.1002/asia.201403152 |
| format | Article |
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Ring ring, ACDE: A direct and short construction of the ACDE ring system of daphenylline has been accomplished from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization, and an intramolecular Friedel–Crafts acylation.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201403152</identifier><identifier>PMID: 25425355</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Acylation ; Aldehydes - chemistry ; alkaloids ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Alkenes - chemistry ; aza-Cope-Mannich reaction ; Catalysis ; Chemistry ; Crown Compounds - chemistry ; Crystallography, X-Ray ; Cyclization ; daphenylline ; Ferric Compounds - chemistry ; Friedel-Crafts acylation ; Molecular Conformation ; Saturn</subject><ispartof>Chemistry, an Asian journal, 2015-02, Vol.10 (2), p.377-382</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4772-e26bff14e0f6b9bf805229463591fc08ddb2fdfe74a3cc257dd94a817d78ccd33</citedby><cites>FETCH-LOGICAL-c4772-e26bff14e0f6b9bf805229463591fc08ddb2fdfe74a3cc257dd94a817d78ccd33</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%2Fasia.201403152$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201403152$$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/25425355$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Wei</creatorcontrib><creatorcontrib>Li, Guo-Ping</creatorcontrib><creatorcontrib>Wang, Shao-Feng</creatorcontrib><creatorcontrib>Shi, Zi-Fa</creatorcontrib><creatorcontrib>Cao, Xiao-Ping</creatorcontrib><title>Direct and Short Construction of the ACDE Ring System of Daphenylline</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization and an intramolecular Friedel–Crafts acylation.
Ring ring, ACDE: A direct and short construction of the ACDE ring system of daphenylline has been accomplished from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization, and an intramolecular Friedel–Crafts acylation.</description><subject>Acylation</subject><subject>Aldehydes - chemistry</subject><subject>alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Alkenes - chemistry</subject><subject>aza-Cope-Mannich reaction</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Crown Compounds - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>daphenylline</subject><subject>Ferric Compounds - chemistry</subject><subject>Friedel-Crafts acylation</subject><subject>Molecular Conformation</subject><subject>Saturn</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtP4zAURi3EiNewZYkisWGTjp9xvKzSUhDVgOiMhp3l-EENaVLsRNB_T6qWCrGZ1b26Ot-nqwPAGYIDBCH-paJXAwwRhQQxvAeOUJ6hlHL0uL_bcX4IjmN8hpBhKPIDcIgZxYwwdgTGIx-sbhNVm2Q2b0KbFE0d29Dp1jd10rikndtkWIzGyYOvn5LZKrZ2sb6P1HJu61VV-dr-BD-cqqI93c4T8Pdq_Ke4Tqd3k5tiOE015RynFmelc4ha6LJSlC7vH8KCZoQJ5DTMjSmxM85yqojWmHFjBFU54obnWhtCTsDlpncZmtfOxlYufNS2qlRtmy5KlDFMcsEQ7dGLb-hz04W6_66nKCeYcCF6arChdGhiDNbJZfALFVYSQbkWLNeC5U5wHzjf1nblwpod_mm0B8QGePOVXf2nTg5nN8Ov5ekm63vJ77usCi8y44Qz-e_3RNLbB3Z_PSnkjHwAhHGU7A</recordid><startdate>201502</startdate><enddate>201502</enddate><creator>Wang, Wei</creator><creator>Li, Guo-Ping</creator><creator>Wang, Shao-Feng</creator><creator>Shi, Zi-Fa</creator><creator>Cao, Xiao-Ping</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>201502</creationdate><title>Direct and Short Construction of the ACDE Ring System of Daphenylline</title><author>Wang, Wei ; Li, Guo-Ping ; Wang, Shao-Feng ; Shi, Zi-Fa ; Cao, Xiao-Ping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4772-e26bff14e0f6b9bf805229463591fc08ddb2fdfe74a3cc257dd94a817d78ccd33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acylation</topic><topic>Aldehydes - chemistry</topic><topic>alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Alkenes - chemistry</topic><topic>aza-Cope-Mannich reaction</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Crown Compounds - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>daphenylline</topic><topic>Ferric Compounds - chemistry</topic><topic>Friedel-Crafts acylation</topic><topic>Molecular Conformation</topic><topic>Saturn</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Wei</creatorcontrib><creatorcontrib>Li, Guo-Ping</creatorcontrib><creatorcontrib>Wang, Shao-Feng</creatorcontrib><creatorcontrib>Shi, Zi-Fa</creatorcontrib><creatorcontrib>Cao, Xiao-Ping</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Wei</au><au>Li, Guo-Ping</au><au>Wang, Shao-Feng</au><au>Shi, Zi-Fa</au><au>Cao, Xiao-Ping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct and Short Construction of the ACDE Ring System of Daphenylline</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2015-02</date><risdate>2015</risdate><volume>10</volume><issue>2</issue><spage>377</spage><epage>382</epage><pages>377-382</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization and an intramolecular Friedel–Crafts acylation.
Ring ring, ACDE: A direct and short construction of the ACDE ring system of daphenylline has been accomplished from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization, and an intramolecular Friedel–Crafts acylation.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25425355</pmid><doi>10.1002/asia.201403152</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | Acylation Aldehydes - chemistry alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Alkenes - chemistry aza-Cope-Mannich reaction Catalysis Chemistry Crown Compounds - chemistry Crystallography, X-Ray Cyclization daphenylline Ferric Compounds - chemistry Friedel-Crafts acylation Molecular Conformation Saturn |
| title | Direct and Short Construction of the ACDE Ring System of Daphenylline |
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