Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals
The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formatio...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2008-09, Vol.73 (18), p.7409-7412 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7412 |
|---|---|
| container_issue | 18 |
| container_start_page | 7409 |
| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Jacobine, Alexander M Lin, Weimin Walls, Bethany Zercher, Charles K |
| description | The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products. |
| doi_str_mv | 10.1021/jo801258h |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_69541945</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>69541945</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-ffe2ec7d009e72da716c2f3cb4dadb5ee87deeb35ad3cfb70ff4030b343bcfb83</originalsourceid><addsrcrecordid>eNpt0M1O3DAUBWALtYKBdsELoGxaiUVa_8R2skRR6SClQ6VStpZjXzOBJAY7QfS5eA-eCaMZDZt6c2X589HVQeiY4G8EU_L91peYUF6u99CCcIpzUeHiA1pgTGnOqGAH6DDGW5wO53wfHZBSVEyKcoFW5z4Meur8mHmXvTznjTaTHyFm0zr4-Wad1Wer_BfYTk9gs8unzib9CFndg37UN_D2bQlDdweT7uMn9NGlAZ-38wj9Pf9xVS_z5vLnRX3W5JqVZMqdAwpGWowrkNRqSYShjpm2sNq2HKCUFqBlXFtmXCuxcwVmuGUFa9O9ZEfo6yb3PviHGeKkhi4a6Hs9gp-jEhUvSFXwBE830AQfYwCn7kM36PBPEazeylO78pI92YbO7QD2XW7bSuDLFuhodO-CHk0Xd45iITApi-TyjeviBE-7dx3ulJBMcnX1-49iTb26Xspr1bznahPTPnMYU3f_WfAVsp2Tug</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>69541945</pqid></control><display><type>article</type><title>Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals</title><source>ACS Publications</source><source>MEDLINE</source><creator>Jacobine, Alexander M ; Lin, Weimin ; Walls, Bethany ; Zercher, Charles K</creator><creatorcontrib>Jacobine, Alexander M ; Lin, Weimin ; Walls, Bethany ; Zercher, Charles K</creatorcontrib><description>The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo801258h</identifier><identifier>PMID: 18693768</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemical synthesis ; 4-Butyrolactone - chemistry ; Cerium - chemistry ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Ketones - chemistry ; Lactones - chemical synthesis ; Lactones - chemistry ; Molecular Conformation ; Organic chemistry ; Oxidation-Reduction ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2008-09, Vol.73 (18), p.7409-7412</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-ffe2ec7d009e72da716c2f3cb4dadb5ee87deeb35ad3cfb70ff4030b343bcfb83</citedby><cites>FETCH-LOGICAL-a381t-ffe2ec7d009e72da716c2f3cb4dadb5ee87deeb35ad3cfb70ff4030b343bcfb83</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/jo801258h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo801258h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20660184$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18693768$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jacobine, Alexander M</creatorcontrib><creatorcontrib>Lin, Weimin</creatorcontrib><creatorcontrib>Walls, Bethany</creatorcontrib><creatorcontrib>Zercher, Charles K</creatorcontrib><title>Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemical synthesis</subject><subject>4-Butyrolactone - chemistry</subject><subject>Cerium - chemistry</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Ketones - chemistry</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - chemistry</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1O3DAUBWALtYKBdsELoGxaiUVa_8R2skRR6SClQ6VStpZjXzOBJAY7QfS5eA-eCaMZDZt6c2X589HVQeiY4G8EU_L91peYUF6u99CCcIpzUeHiA1pgTGnOqGAH6DDGW5wO53wfHZBSVEyKcoFW5z4Meur8mHmXvTznjTaTHyFm0zr4-Wad1Wer_BfYTk9gs8unzib9CFndg37UN_D2bQlDdweT7uMn9NGlAZ-38wj9Pf9xVS_z5vLnRX3W5JqVZMqdAwpGWowrkNRqSYShjpm2sNq2HKCUFqBlXFtmXCuxcwVmuGUFa9O9ZEfo6yb3PviHGeKkhi4a6Hs9gp-jEhUvSFXwBE830AQfYwCn7kM36PBPEazeylO78pI92YbO7QD2XW7bSuDLFuhodO-CHk0Xd45iITApi-TyjeviBE-7dx3ulJBMcnX1-49iTb26Xspr1bznahPTPnMYU3f_WfAVsp2Tug</recordid><startdate>20080919</startdate><enddate>20080919</enddate><creator>Jacobine, Alexander M</creator><creator>Lin, Weimin</creator><creator>Walls, Bethany</creator><creator>Zercher, Charles K</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20080919</creationdate><title>Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals</title><author>Jacobine, Alexander M ; Lin, Weimin ; Walls, Bethany ; Zercher, Charles K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-ffe2ec7d009e72da716c2f3cb4dadb5ee87deeb35ad3cfb70ff4030b343bcfb83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - chemical synthesis</topic><topic>4-Butyrolactone - chemistry</topic><topic>Cerium - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Ketones - chemistry</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - chemistry</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jacobine, Alexander M</creatorcontrib><creatorcontrib>Lin, Weimin</creatorcontrib><creatorcontrib>Walls, Bethany</creatorcontrib><creatorcontrib>Zercher, Charles K</creatorcontrib><collection>Istex</collection><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>Jacobine, Alexander M</au><au>Lin, Weimin</au><au>Walls, Bethany</au><au>Zercher, Charles K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-09-19</date><risdate>2008</risdate><volume>73</volume><issue>18</issue><spage>7409</spage><epage>7412</epage><pages>7409-7412</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18693768</pmid><doi>10.1021/jo801258h</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2008-09, Vol.73 (18), p.7409-7412 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69541945 |
| source | ACS Publications; MEDLINE |
| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemical synthesis 4-Butyrolactone - chemistry Cerium - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Ketones - chemistry Lactones - chemical synthesis Lactones - chemistry Molecular Conformation Organic chemistry Oxidation-Reduction Preparations and properties Stereoisomerism |
| title | Formation of γ-Lactones through CAN-Mediated Oxidative Cleavage of Hemiketals |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T04%3A35%3A53IST&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=Formation%20of%20%CE%B3-Lactones%20through%20CAN-Mediated%20Oxidative%20Cleavage%20of%20Hemiketals&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Jacobine,%20Alexander%20M&rft.date=2008-09-19&rft.volume=73&rft.issue=18&rft.spage=7409&rft.epage=7412&rft.pages=7409-7412&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo801258h&rft_dat=%3Cproquest_cross%3E69541945%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=69541945&rft_id=info:pmid/18693768&rfr_iscdi=true |