Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist
A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium fol...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2001-10, Vol.3 (21), p.3357-3360 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3360 |
|---|---|
| container_issue | 21 |
| container_start_page | 3357 |
| container_title | Organic letters |
| container_volume | 3 |
| creator | Song, Zhiguo J Zhao, Matthew Frey, Lisa Li, Jing Tan, Lushi Chen, Cheng Y Tschaen, David M Tillyer, Richard Grabowski, Edward J. J Volante, Ralph Reider, Paul J Kato, Yoshiaki Okada, Shigemitsu Nemoto, Takayuki Sato, Hiroki Akao, Atsushi Mase, Toshiaki |
| description | A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers. |
| doi_str_mv | 10.1021/ol016601s |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72186596</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72186596</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-a66ef01b87fc9320548f5cce9425bc3c09890048f49630c435dddc11fd59a9143</originalsourceid><addsrcrecordid>eNptkM1OwzAQhC0EoqVw4AWQLyB6KKzjOImPUVV-pEogWs6R62wgVRIX20Hq22PUqlw4zWr225F2CLlkcMcgYvemAZYkwNwRGTIR8UkKIjo-zAkMyJlzawAWHHlKBkFlnHE-JMtXq7SvtWpo7rZti97Wmi62nf9EVztqKqroAhsM0DfSWVeasGnqjub0DTVuvLH0drbMxzTvvPowXe38OTmpVOPwYq8j8v4wW06fJvOXx-dpPp8onko_UUmCFbBVllZa8ghEnFVCa5RxJFaaa5CZBAhmLBMOOuaiLEvNWFUKqSSL-Yjc7HI31nz16HzR1k5j06gOTe-KNGJZIsLxiIx3oLbGOYtVsbF1q-y2YFD8VlgcKgzs1T60X7VY_pH7zgJwvQOUdsXa9LYLP_4T9APF-Xa-</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72186596</pqid></control><display><type>article</type><title>Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist</title><source>ACS Publications</source><source>MEDLINE</source><creator>Song, Zhiguo J ; Zhao, Matthew ; Frey, Lisa ; Li, Jing ; Tan, Lushi ; Chen, Cheng Y ; Tschaen, David M ; Tillyer, Richard ; Grabowski, Edward J. J ; Volante, Ralph ; Reider, Paul J ; Kato, Yoshiaki ; Okada, Shigemitsu ; Nemoto, Takayuki ; Sato, Hiroki ; Akao, Atsushi ; Mase, Toshiaki</creator><creatorcontrib>Song, Zhiguo J ; Zhao, Matthew ; Frey, Lisa ; Li, Jing ; Tan, Lushi ; Chen, Cheng Y ; Tschaen, David M ; Tillyer, Richard ; Grabowski, Edward J. J ; Volante, Ralph ; Reider, Paul J ; Kato, Yoshiaki ; Okada, Shigemitsu ; Nemoto, Takayuki ; Sato, Hiroki ; Akao, Atsushi ; Mase, Toshiaki</creatorcontrib><description>A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol016601s</identifier><identifier>PMID: 11594833</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antihypertensive Agents - chemical synthesis ; Benzofurans - chemical synthesis ; Endothelin Receptor Antagonists ; Pyridines - chemical synthesis ; Receptor, Endothelin A</subject><ispartof>Organic letters, 2001-10, Vol.3 (21), p.3357-3360</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-a66ef01b87fc9320548f5cce9425bc3c09890048f49630c435dddc11fd59a9143</citedby><cites>FETCH-LOGICAL-a379t-a66ef01b87fc9320548f5cce9425bc3c09890048f49630c435dddc11fd59a9143</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol016601s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol016601s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11594833$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Song, Zhiguo J</creatorcontrib><creatorcontrib>Zhao, Matthew</creatorcontrib><creatorcontrib>Frey, Lisa</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Tan, Lushi</creatorcontrib><creatorcontrib>Chen, Cheng Y</creatorcontrib><creatorcontrib>Tschaen, David M</creatorcontrib><creatorcontrib>Tillyer, Richard</creatorcontrib><creatorcontrib>Grabowski, Edward J. J</creatorcontrib><creatorcontrib>Volante, Ralph</creatorcontrib><creatorcontrib>Reider, Paul J</creatorcontrib><creatorcontrib>Kato, Yoshiaki</creatorcontrib><creatorcontrib>Okada, Shigemitsu</creatorcontrib><creatorcontrib>Nemoto, Takayuki</creatorcontrib><creatorcontrib>Sato, Hiroki</creatorcontrib><creatorcontrib>Akao, Atsushi</creatorcontrib><creatorcontrib>Mase, Toshiaki</creatorcontrib><title>Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.</description><subject>Antihypertensive Agents - chemical synthesis</subject><subject>Benzofurans - chemical synthesis</subject><subject>Endothelin Receptor Antagonists</subject><subject>Pyridines - chemical synthesis</subject><subject>Receptor, Endothelin A</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1OwzAQhC0EoqVw4AWQLyB6KKzjOImPUVV-pEogWs6R62wgVRIX20Hq22PUqlw4zWr225F2CLlkcMcgYvemAZYkwNwRGTIR8UkKIjo-zAkMyJlzawAWHHlKBkFlnHE-JMtXq7SvtWpo7rZti97Wmi62nf9EVztqKqroAhsM0DfSWVeasGnqjub0DTVuvLH0drbMxzTvvPowXe38OTmpVOPwYq8j8v4wW06fJvOXx-dpPp8onko_UUmCFbBVllZa8ghEnFVCa5RxJFaaa5CZBAhmLBMOOuaiLEvNWFUKqSSL-Yjc7HI31nz16HzR1k5j06gOTe-KNGJZIsLxiIx3oLbGOYtVsbF1q-y2YFD8VlgcKgzs1T60X7VY_pH7zgJwvQOUdsXa9LYLP_4T9APF-Xa-</recordid><startdate>20011018</startdate><enddate>20011018</enddate><creator>Song, Zhiguo J</creator><creator>Zhao, Matthew</creator><creator>Frey, Lisa</creator><creator>Li, Jing</creator><creator>Tan, Lushi</creator><creator>Chen, Cheng Y</creator><creator>Tschaen, David M</creator><creator>Tillyer, Richard</creator><creator>Grabowski, Edward J. J</creator><creator>Volante, Ralph</creator><creator>Reider, Paul J</creator><creator>Kato, Yoshiaki</creator><creator>Okada, Shigemitsu</creator><creator>Nemoto, Takayuki</creator><creator>Sato, Hiroki</creator><creator>Akao, Atsushi</creator><creator>Mase, Toshiaki</creator><general>American Chemical Society</general><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>7X8</scope></search><sort><creationdate>20011018</creationdate><title>Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist</title><author>Song, Zhiguo J ; Zhao, Matthew ; Frey, Lisa ; Li, Jing ; Tan, Lushi ; Chen, Cheng Y ; Tschaen, David M ; Tillyer, Richard ; Grabowski, Edward J. J ; Volante, Ralph ; Reider, Paul J ; Kato, Yoshiaki ; Okada, Shigemitsu ; Nemoto, Takayuki ; Sato, Hiroki ; Akao, Atsushi ; Mase, Toshiaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-a66ef01b87fc9320548f5cce9425bc3c09890048f49630c435dddc11fd59a9143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Antihypertensive Agents - chemical synthesis</topic><topic>Benzofurans - chemical synthesis</topic><topic>Endothelin Receptor Antagonists</topic><topic>Pyridines - chemical synthesis</topic><topic>Receptor, Endothelin A</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Zhiguo J</creatorcontrib><creatorcontrib>Zhao, Matthew</creatorcontrib><creatorcontrib>Frey, Lisa</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Tan, Lushi</creatorcontrib><creatorcontrib>Chen, Cheng Y</creatorcontrib><creatorcontrib>Tschaen, David M</creatorcontrib><creatorcontrib>Tillyer, Richard</creatorcontrib><creatorcontrib>Grabowski, Edward J. J</creatorcontrib><creatorcontrib>Volante, Ralph</creatorcontrib><creatorcontrib>Reider, Paul J</creatorcontrib><creatorcontrib>Kato, Yoshiaki</creatorcontrib><creatorcontrib>Okada, Shigemitsu</creatorcontrib><creatorcontrib>Nemoto, Takayuki</creatorcontrib><creatorcontrib>Sato, Hiroki</creatorcontrib><creatorcontrib>Akao, Atsushi</creatorcontrib><creatorcontrib>Mase, Toshiaki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Song, Zhiguo J</au><au>Zhao, Matthew</au><au>Frey, Lisa</au><au>Li, Jing</au><au>Tan, Lushi</au><au>Chen, Cheng Y</au><au>Tschaen, David M</au><au>Tillyer, Richard</au><au>Grabowski, Edward J. J</au><au>Volante, Ralph</au><au>Reider, Paul J</au><au>Kato, Yoshiaki</au><au>Okada, Shigemitsu</au><au>Nemoto, Takayuki</au><au>Sato, Hiroki</au><au>Akao, Atsushi</au><au>Mase, Toshiaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2001-10-18</date><risdate>2001</risdate><volume>3</volume><issue>21</issue><spage>3357</spage><epage>3360</epage><pages>3357-3360</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11594833</pmid><doi>10.1021/ol016601s</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2001-10, Vol.3 (21), p.3357-3360 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72186596 |
| source | ACS Publications; MEDLINE |
| subjects | Antihypertensive Agents - chemical synthesis Benzofurans - chemical synthesis Endothelin Receptor Antagonists Pyridines - chemical synthesis Receptor, Endothelin A |
| title | Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T22%3A41%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Practical%20Asymmetric%20Synthesis%20of%20a%20Selective%20Endothelin%20A%20Receptor%20(ETA)%20Antagonist&rft.jtitle=Organic%20letters&rft.au=Song,%20Zhiguo%20J&rft.date=2001-10-18&rft.volume=3&rft.issue=21&rft.spage=3357&rft.epage=3360&rft.pages=3357-3360&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol016601s&rft_dat=%3Cproquest_cross%3E72186596%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72186596&rft_id=info:pmid/11594833&rfr_iscdi=true |