Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid
The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displace...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2005-05, Vol.7 (10), p.1947-1950 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1950 |
|---|---|
| container_issue | 10 |
| container_start_page | 1947 |
| container_title | Organic letters |
| container_volume | 7 |
| creator | Houpis, Ioannis N Patterson, Lawrence E Alt, Charles A Rizzo, John R Zhang, Tony Y Haurez, Michael |
| description | The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization of the two epimerizable chiral centers. |
| doi_str_mv | 10.1021/ol050367e |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67801164</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67801164</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-207a888ebc5bc073d61da6ea382ae3340246d31f6aadf9e5844b50066a547c293</originalsourceid><addsrcrecordid>eNptkUtLAzEQgIMovg_-AclF0cNqHrvZ7XFpfUHBYvW8TLOzGtlNarIt9G_4i01p0YsQSJj58g0zQ8gZZzecCX7rWpYxqXLcIYc8EzLJWSZ2f9-KHZCjED4Z4zEy2CcHPCtyxYQ6JN_Tle0_MJhAXUMnk_KFlu_OmtDTpQFahlXXYe-Npo-r2rt3tNAbZ9cw0KGxFrqYK7Wp6Qi9WcbsEinYmk579OjCHLVpIjIyYd6Cxg5tv_59Nb1ORDL8aJ1383iidCs6IXsNtAFPt_cxebu_ex0-JuPnh6dhOU5ActknguVQFAXOdDbTLJe14jUoBFkIQClTJlJVS94ogLoZYFak6SxjTCnI0lyLgTwmlxtvLP-1wNBXnQka2xYsukWoVF7Egak0gtcbUHsXgsemmnvTgV9VnFXrBVS_C4js-Va6mHVY_5HbiUfgYgOADtWnW3gbe_xH9AMwPo1V</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67801164</pqid></control><display><type>article</type><title>Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Houpis, Ioannis N ; Patterson, Lawrence E ; Alt, Charles A ; Rizzo, John R ; Zhang, Tony Y ; Haurez, Michael</creator><creatorcontrib>Houpis, Ioannis N ; Patterson, Lawrence E ; Alt, Charles A ; Rizzo, John R ; Zhang, Tony Y ; Haurez, Michael</creatorcontrib><description>The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization of the two epimerizable chiral centers.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol050367e</identifier><identifier>PMID: 15876026</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cinnamates - chemistry ; Combinatorial Chemistry Techniques ; Hydrogenation ; Molecular Structure ; PPAR alpha - agonists ; PPAR gamma - agonists ; Propionates - chemical synthesis ; Propionates - chemistry ; Propionates - pharmacology ; Stereoisomerism</subject><ispartof>Organic letters, 2005-05, Vol.7 (10), p.1947-1950</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-207a888ebc5bc073d61da6ea382ae3340246d31f6aadf9e5844b50066a547c293</citedby><cites>FETCH-LOGICAL-a313t-207a888ebc5bc073d61da6ea382ae3340246d31f6aadf9e5844b50066a547c293</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/ol050367e$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol050367e$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15876026$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Houpis, Ioannis N</creatorcontrib><creatorcontrib>Patterson, Lawrence E</creatorcontrib><creatorcontrib>Alt, Charles A</creatorcontrib><creatorcontrib>Rizzo, John R</creatorcontrib><creatorcontrib>Zhang, Tony Y</creatorcontrib><creatorcontrib>Haurez, Michael</creatorcontrib><title>Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization of the two epimerizable chiral centers.</description><subject>Cinnamates - chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Hydrogenation</subject><subject>Molecular Structure</subject><subject>PPAR alpha - agonists</subject><subject>PPAR gamma - agonists</subject><subject>Propionates - chemical synthesis</subject><subject>Propionates - chemistry</subject><subject>Propionates - pharmacology</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkUtLAzEQgIMovg_-AclF0cNqHrvZ7XFpfUHBYvW8TLOzGtlNarIt9G_4i01p0YsQSJj58g0zQ8gZZzecCX7rWpYxqXLcIYc8EzLJWSZ2f9-KHZCjED4Z4zEy2CcHPCtyxYQ6JN_Tle0_MJhAXUMnk_KFlu_OmtDTpQFahlXXYe-Npo-r2rt3tNAbZ9cw0KGxFrqYK7Wp6Qi9WcbsEinYmk579OjCHLVpIjIyYd6Cxg5tv_59Nb1ORDL8aJ1383iidCs6IXsNtAFPt_cxebu_ex0-JuPnh6dhOU5ActknguVQFAXOdDbTLJe14jUoBFkIQClTJlJVS94ogLoZYFak6SxjTCnI0lyLgTwmlxtvLP-1wNBXnQka2xYsukWoVF7Egak0gtcbUHsXgsemmnvTgV9VnFXrBVS_C4js-Va6mHVY_5HbiUfgYgOADtWnW3gbe_xH9AMwPo1V</recordid><startdate>20050512</startdate><enddate>20050512</enddate><creator>Houpis, Ioannis N</creator><creator>Patterson, Lawrence E</creator><creator>Alt, Charles A</creator><creator>Rizzo, John R</creator><creator>Zhang, Tony Y</creator><creator>Haurez, Michael</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>20050512</creationdate><title>Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid</title><author>Houpis, Ioannis N ; Patterson, Lawrence E ; Alt, Charles A ; Rizzo, John R ; Zhang, Tony Y ; Haurez, Michael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-207a888ebc5bc073d61da6ea382ae3340246d31f6aadf9e5844b50066a547c293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Cinnamates - chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Hydrogenation</topic><topic>Molecular Structure</topic><topic>PPAR alpha - agonists</topic><topic>PPAR gamma - agonists</topic><topic>Propionates - chemical synthesis</topic><topic>Propionates - chemistry</topic><topic>Propionates - pharmacology</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Houpis, Ioannis N</creatorcontrib><creatorcontrib>Patterson, Lawrence E</creatorcontrib><creatorcontrib>Alt, Charles A</creatorcontrib><creatorcontrib>Rizzo, John R</creatorcontrib><creatorcontrib>Zhang, Tony Y</creatorcontrib><creatorcontrib>Haurez, Michael</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>Houpis, Ioannis N</au><au>Patterson, Lawrence E</au><au>Alt, Charles A</au><au>Rizzo, John R</au><au>Zhang, Tony Y</au><au>Haurez, Michael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-05-12</date><risdate>2005</risdate><volume>7</volume><issue>10</issue><spage>1947</spage><epage>1950</epage><pages>1947-1950</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization of the two epimerizable chiral centers.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15876026</pmid><doi>10.1021/ol050367e</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2005-05, Vol.7 (10), p.1947-1950 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67801164 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Cinnamates - chemistry Combinatorial Chemistry Techniques Hydrogenation Molecular Structure PPAR alpha - agonists PPAR gamma - agonists Propionates - chemical synthesis Propionates - chemistry Propionates - pharmacology Stereoisomerism |
| title | Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T06%3A35%3A08IST&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=Synthesis%20of%20PPAR%20Agonist%20via%20Asymmetric%20Hydrogenation%20of%20a%20Cinnamic%20Acid%20Derivative%20and%20Stereospecific%20Displacement%20of%20(S)-2-Chloropropionic%20Acid&rft.jtitle=Organic%20letters&rft.au=Houpis,%20Ioannis%20N&rft.date=2005-05-12&rft.volume=7&rft.issue=10&rft.spage=1947&rft.epage=1950&rft.pages=1947-1950&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol050367e&rft_dat=%3Cproquest_cross%3E67801164%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=67801164&rft_id=info:pmid/15876026&rfr_iscdi=true |