Strategies for the Total Synthesis of Clavicipitic Acid
Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized i...
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| Veröffentlicht in: | Chemistry : a European journal 2016-04, Vol.22 (16), p.5468-5477 |
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| container_title | Chemistry : a European journal |
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| creator | Ito, Mamoru Tahara, Yu-ki Shibata, Takanori |
| description | Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates
Intermediate is key: Clavicipitic acid is an ergot alkaloid with a unique tricyclic azepinoindole skeleton that has attracted many synthetic chemists. This Minireview summarizes the strategies for the total synthesis from the point of two key intermediates: 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives. |
| doi_str_mv | 10.1002/chem.201505014 |
| format | Article |
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Intermediate is key: Clavicipitic acid is an ergot alkaloid with a unique tricyclic azepinoindole skeleton that has attracted many synthetic chemists. This Minireview summarizes the strategies for the total synthesis from the point of two key intermediates: 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201505014</identifier><identifier>PMID: 26822254</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Alkaloids ; azepinoindole ; Catalysis ; Chemistry ; Chemists ; clavicipitic acid ; Derivatives ; Ergot Alkaloids - chemical synthesis ; Ergot Alkaloids - chemistry ; gramine ; Molecular Structure ; Stereoisomerism ; Strain ; Strategy ; Synthesis ; total synthesis ; Tryptophan ; Tryptophan - analogs & derivatives ; Tryptophan - chemistry</subject><ispartof>Chemistry : a European journal, 2016-04, Vol.22 (16), p.5468-5477</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-c6174-dabf6be1db0119ccdfbcbe4c303a40ce7332fe9fd5fad735fe4cac114ac4166c3</citedby><cites>FETCH-LOGICAL-c6174-dabf6be1db0119ccdfbcbe4c303a40ce7332fe9fd5fad735fe4cac114ac4166c3</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.201505014$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201505014$$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/26822254$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ito, Mamoru</creatorcontrib><creatorcontrib>Tahara, Yu-ki</creatorcontrib><creatorcontrib>Shibata, Takanori</creatorcontrib><title>Strategies for the Total Synthesis of Clavicipitic Acid</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates
Intermediate is key: Clavicipitic acid is an ergot alkaloid with a unique tricyclic azepinoindole skeleton that has attracted many synthetic chemists. This Minireview summarizes the strategies for the total synthesis from the point of two key intermediates: 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives.</description><subject>Alkaloids</subject><subject>azepinoindole</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemists</subject><subject>clavicipitic acid</subject><subject>Derivatives</subject><subject>Ergot Alkaloids - chemical synthesis</subject><subject>Ergot Alkaloids - chemistry</subject><subject>gramine</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><subject>Strain</subject><subject>Strategy</subject><subject>Synthesis</subject><subject>total synthesis</subject><subject>Tryptophan</subject><subject>Tryptophan - analogs & derivatives</subject><subject>Tryptophan - chemistry</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1P4zAURS0EGkpntixRJDZsUvz8WS9RVCgaBsSUGZaW49hgSJtip0D_PakKFWKD3sJ68rlHehehfcADwJgc23s3HRAMHHMMbAv1gBPIqRR8G_WwYjIXnKpdtJfSA8ZYCUp_oF0ihoQQznpITtpoWncXXMp8E7P23mU3TWvqbLKcdUsKKWt8VtTmOdgwD22w2YkN1U-0402d3K_3t4_-nY5uinF-cXV2Xpxc5FaAZHllSi9KB1WJAZS1lS9t6ZilmBqGrZOUEu-Ur7g3laTcd3_GAjBjGQhhaR8drb3z2DwtXGr1NCTr6trMXLNIGoa4G8oI_x6VQ8xBKs469PAL-tAs4qw7pKOkkoQxtaIGa8rGJqXovJ7HMDVxqQHrVft61b7etN8FDt61i3Lqqg3-UXcHqDXwEmq3_Eani_Hoz2d5vs6G1LrXTdbERy0klVzfXp5pQou_1_B7rP_TN594nxM</recordid><startdate>20160411</startdate><enddate>20160411</enddate><creator>Ito, Mamoru</creator><creator>Tahara, Yu-ki</creator><creator>Shibata, Takanori</creator><general>Blackwell Publishing Ltd</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160411</creationdate><title>Strategies for the Total Synthesis of Clavicipitic Acid</title><author>Ito, Mamoru ; Tahara, Yu-ki ; Shibata, Takanori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6174-dabf6be1db0119ccdfbcbe4c303a40ce7332fe9fd5fad735fe4cac114ac4166c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alkaloids</topic><topic>azepinoindole</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemists</topic><topic>clavicipitic acid</topic><topic>Derivatives</topic><topic>Ergot Alkaloids - chemical synthesis</topic><topic>Ergot Alkaloids - chemistry</topic><topic>gramine</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><topic>Strain</topic><topic>Strategy</topic><topic>Synthesis</topic><topic>total synthesis</topic><topic>Tryptophan</topic><topic>Tryptophan - analogs & derivatives</topic><topic>Tryptophan - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ito, Mamoru</creatorcontrib><creatorcontrib>Tahara, Yu-ki</creatorcontrib><creatorcontrib>Shibata, Takanori</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>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>Ito, Mamoru</au><au>Tahara, Yu-ki</au><au>Shibata, Takanori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Strategies for the Total Synthesis of Clavicipitic Acid</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-04-11</date><risdate>2016</risdate><volume>22</volume><issue>16</issue><spage>5468</spage><epage>5477</epage><pages>5468-5477</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates
Intermediate is key: Clavicipitic acid is an ergot alkaloid with a unique tricyclic azepinoindole skeleton that has attracted many synthetic chemists. This Minireview summarizes the strategies for the total synthesis from the point of two key intermediates: 4‐substituted gramine derivatives and 4‐substituted tryptophan derivatives.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26822254</pmid><doi>10.1002/chem.201505014</doi><tpages>10</tpages></addata></record> |
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| source | Wiley-Blackwell Journals; MEDLINE |
| subjects | Alkaloids azepinoindole Catalysis Chemistry Chemists clavicipitic acid Derivatives Ergot Alkaloids - chemical synthesis Ergot Alkaloids - chemistry gramine Molecular Structure Stereoisomerism Strain Strategy Synthesis total synthesis Tryptophan Tryptophan - analogs & derivatives Tryptophan - chemistry |
| title | Strategies for the Total Synthesis of Clavicipitic Acid |
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