Total Synthesis of Pteridic Acids A and B
The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively.
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2009-08, Vol.74 (15), p.5584-5589 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5589 |
|---|---|
| container_issue | 15 |
| container_start_page | 5584 |
| container_title | Journal of organic chemistry |
| container_volume | 74 |
| creator | Dias, Luiz C Salles, Airton G |
| description | The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively. |
| doi_str_mv | 10.1021/jo9010365 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_733575753</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>733575753</sourcerecordid><originalsourceid>FETCH-LOGICAL-a344t-90d375232b0cc63500cbdff220b530c31e71afaf0bf0fe785509a1734be996fb3</originalsourceid><addsrcrecordid>eNpt0D1PwzAQBmALgWgpDPwB5AWhDoGzL47rsVR8SZVAosyR49giVZoUOxn67zFq1C74Bi-P3ju9hFwzuGfA2cO6VcAAM3FCxkxwSDIF6SkZA3CeIM9wRC5CWEN8QohzMmJKSC6UGJPpqu10TT93TfdtQxVo6-hHZ31VVobOTVUGOqe6KenjJTlzug72avgn5Ov5abV4TZbvL2-L-TLRmKZdoqBEKTjyAozJUACYonSOcygEgkFmJdNOOygcOCtnQoDSTGJaWKUyV-CE3O1zt7796W3o8k0VjK1r3di2D7lEFDIORjndS-PbELx1-dZXG-13OYP8r5j8UEy0N0NqX2xseZRDExHcDkAHo2vndWOqcHDx_plEjkenTYj5vW9iGf8s_AV9bHMc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>733575753</pqid></control><display><type>article</type><title>Total Synthesis of Pteridic Acids A and B</title><source>MEDLINE</source><source>ACS Publications</source><creator>Dias, Luiz C ; Salles, Airton G</creator><creatorcontrib>Dias, Luiz C ; Salles, Airton G</creatorcontrib><description>The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo9010365</identifier><identifier>PMID: 19572595</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heptanoic Acids - chemical synthesis ; Heptanoic Acids - chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Molecular Conformation ; Organic chemistry ; Preparations and properties ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2009-08, Vol.74 (15), p.5584-5589</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-90d375232b0cc63500cbdff220b530c31e71afaf0bf0fe785509a1734be996fb3</citedby><cites>FETCH-LOGICAL-a344t-90d375232b0cc63500cbdff220b530c31e71afaf0bf0fe785509a1734be996fb3</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/jo9010365$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo9010365$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22087323$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19572595$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dias, Luiz C</creatorcontrib><creatorcontrib>Salles, Airton G</creatorcontrib><title>Total Synthesis of Pteridic Acids A and B</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heptanoic Acids - chemical synthesis</subject><subject>Heptanoic Acids - chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0D1PwzAQBmALgWgpDPwB5AWhDoGzL47rsVR8SZVAosyR49giVZoUOxn67zFq1C74Bi-P3ju9hFwzuGfA2cO6VcAAM3FCxkxwSDIF6SkZA3CeIM9wRC5CWEN8QohzMmJKSC6UGJPpqu10TT93TfdtQxVo6-hHZ31VVobOTVUGOqe6KenjJTlzug72avgn5Ov5abV4TZbvL2-L-TLRmKZdoqBEKTjyAozJUACYonSOcygEgkFmJdNOOygcOCtnQoDSTGJaWKUyV-CE3O1zt7796W3o8k0VjK1r3di2D7lEFDIORjndS-PbELx1-dZXG-13OYP8r5j8UEy0N0NqX2xseZRDExHcDkAHo2vndWOqcHDx_plEjkenTYj5vW9iGf8s_AV9bHMc</recordid><startdate>20090807</startdate><enddate>20090807</enddate><creator>Dias, Luiz C</creator><creator>Salles, Airton G</creator><general>American Chemical Society</general><scope>IQODW</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>7X8</scope></search><sort><creationdate>20090807</creationdate><title>Total Synthesis of Pteridic Acids A and B</title><author>Dias, Luiz C ; Salles, Airton G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-90d375232b0cc63500cbdff220b530c31e71afaf0bf0fe785509a1734be996fb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heptanoic Acids - chemical synthesis</topic><topic>Heptanoic Acids - chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dias, Luiz C</creatorcontrib><creatorcontrib>Salles, Airton G</creatorcontrib><collection>Pascal-Francis</collection><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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dias, Luiz C</au><au>Salles, Airton G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Pteridic Acids A and B</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-08-07</date><risdate>2009</risdate><volume>74</volume><issue>15</issue><spage>5584</spage><epage>5589</epage><pages>5584-5589</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19572595</pmid><doi>10.1021/jo9010365</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2009-08, Vol.74 (15), p.5584-5589 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733575753 |
| source | MEDLINE; ACS Publications |
| subjects | Chemistry Exact sciences and technology Heptanoic Acids - chemical synthesis Heptanoic Acids - chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Conformation Organic chemistry Preparations and properties Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism |
| title | Total Synthesis of Pteridic Acids A and B |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T14%3A15%3A46IST&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=Total%20Synthesis%20of%20Pteridic%20Acids%20A%20and%20B&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Dias,%20Luiz%20C&rft.date=2009-08-07&rft.volume=74&rft.issue=15&rft.spage=5584&rft.epage=5589&rft.pages=5584-5589&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo9010365&rft_dat=%3Cproquest_cross%3E733575753%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=733575753&rft_id=info:pmid/19572595&rfr_iscdi=true |