Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy
Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene ring-closing metathesis (RCM) strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2023-03, Vol.25 (10), p.1633-1637 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1637 |
|---|---|
| container_issue | 10 |
| container_start_page | 1633 |
| container_title | Organic letters |
| container_volume | 25 |
| creator | Sit, Man Ki Cao, Hui Hui Wu, Yan-Dong Yip, Tsz Chun Bendel, Lars Eric Zhang, Wen Dai, Wei-Min |
| description | Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene ring-closing metathesis (RCM) strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides. |
| doi_str_mv | 10.1021/acs.orglett.3c00106 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2779348753</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2779348753</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-c37b8be5178b2bdf0416149caaed4475fe05e11c80c630293c904b2c050218c13</originalsourceid><addsrcrecordid>eNp9kEtOwzAQhi0EoqVwAiSUJZu0fsR5LFEoD6kVEoV15DiTksqNi-0gdccduCEnwaWhS1Yztr_5rfkQuiR4TDAlEyHtWJulAufGTGJMcHyEhoRTFiaY0-NDH-MBOrN25RF_k52iAYtTijlhQ1Qvtq17A9vYQNeB74K5kEYrIZ1uIci1gd-XuVAONlo1lT9_NCIQwW0DLXx_fk0999y0yzBX2voazMGJPnPhjHCw3J6jk1ooCxd9HaHXu-lL_hDOnu4f85tZKFjEXShZUqYlcJKkJS2rGkckJlEmhYAqihJeA-ZAiEyxjBmmGZMZjkoqMfdCUknYCF3vczdGv3dgXbFurASlRAu6swVNkoxFacKZR9ke9etaa6AuNqZZC7MtCC52ggsvuOgFF71gP3XVf9CVa6gOM39GPTDZA7vple5M6_f9N_IHmYiK3g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2779348753</pqid></control><display><type>article</type><title>Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy</title><source>ACS Publications</source><creator>Sit, Man Ki ; Cao, Hui Hui ; Wu, Yan-Dong ; Yip, Tsz Chun ; Bendel, Lars Eric ; Zhang, Wen ; Dai, Wei-Min</creator><creatorcontrib>Sit, Man Ki ; Cao, Hui Hui ; Wu, Yan-Dong ; Yip, Tsz Chun ; Bendel, Lars Eric ; Zhang, Wen ; Dai, Wei-Min</creatorcontrib><description>Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene ring-closing metathesis (RCM) strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c00106</identifier><identifier>PMID: 36820513</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2023-03, Vol.25 (10), p.1633-1637</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-c37b8be5178b2bdf0416149caaed4475fe05e11c80c630293c904b2c050218c13</citedby><cites>FETCH-LOGICAL-a345t-c37b8be5178b2bdf0416149caaed4475fe05e11c80c630293c904b2c050218c13</cites><orcidid>0000-0003-1465-2782 ; 0000-0003-4504-7438 ; 0000-0002-2078-5381 ; 0000-0001-5297-4702 ; 0000-0003-0589-7155 ; 0000-0001-6430-1169 ; 0000-0001-5688-7606</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.3c00106$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c00106$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36820513$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sit, Man Ki</creatorcontrib><creatorcontrib>Cao, Hui Hui</creatorcontrib><creatorcontrib>Wu, Yan-Dong</creatorcontrib><creatorcontrib>Yip, Tsz Chun</creatorcontrib><creatorcontrib>Bendel, Lars Eric</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Dai, Wei-Min</creatorcontrib><title>Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene ring-closing metathesis (RCM) strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOwzAQhi0EoqVwAiSUJZu0fsR5LFEoD6kVEoV15DiTksqNi-0gdccduCEnwaWhS1Yztr_5rfkQuiR4TDAlEyHtWJulAufGTGJMcHyEhoRTFiaY0-NDH-MBOrN25RF_k52iAYtTijlhQ1Qvtq17A9vYQNeB74K5kEYrIZ1uIci1gd-XuVAONlo1lT9_NCIQwW0DLXx_fk0999y0yzBX2voazMGJPnPhjHCw3J6jk1ooCxd9HaHXu-lL_hDOnu4f85tZKFjEXShZUqYlcJKkJS2rGkckJlEmhYAqihJeA-ZAiEyxjBmmGZMZjkoqMfdCUknYCF3vczdGv3dgXbFurASlRAu6swVNkoxFacKZR9ke9etaa6AuNqZZC7MtCC52ggsvuOgFF71gP3XVf9CVa6gOM39GPTDZA7vple5M6_f9N_IHmYiK3g</recordid><startdate>20230317</startdate><enddate>20230317</enddate><creator>Sit, Man Ki</creator><creator>Cao, Hui Hui</creator><creator>Wu, Yan-Dong</creator><creator>Yip, Tsz Chun</creator><creator>Bendel, Lars Eric</creator><creator>Zhang, Wen</creator><creator>Dai, Wei-Min</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1465-2782</orcidid><orcidid>https://orcid.org/0000-0003-4504-7438</orcidid><orcidid>https://orcid.org/0000-0002-2078-5381</orcidid><orcidid>https://orcid.org/0000-0001-5297-4702</orcidid><orcidid>https://orcid.org/0000-0003-0589-7155</orcidid><orcidid>https://orcid.org/0000-0001-6430-1169</orcidid><orcidid>https://orcid.org/0000-0001-5688-7606</orcidid></search><sort><creationdate>20230317</creationdate><title>Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy</title><author>Sit, Man Ki ; Cao, Hui Hui ; Wu, Yan-Dong ; Yip, Tsz Chun ; Bendel, Lars Eric ; Zhang, Wen ; Dai, Wei-Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-c37b8be5178b2bdf0416149caaed4475fe05e11c80c630293c904b2c050218c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sit, Man Ki</creatorcontrib><creatorcontrib>Cao, Hui Hui</creatorcontrib><creatorcontrib>Wu, Yan-Dong</creatorcontrib><creatorcontrib>Yip, Tsz Chun</creatorcontrib><creatorcontrib>Bendel, Lars Eric</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Dai, Wei-Min</creatorcontrib><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>Sit, Man Ki</au><au>Cao, Hui Hui</au><au>Wu, Yan-Dong</au><au>Yip, Tsz Chun</au><au>Bendel, Lars Eric</au><au>Zhang, Wen</au><au>Dai, Wei-Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2023-03-17</date><risdate>2023</risdate><volume>25</volume><issue>10</issue><spage>1633</spage><epage>1637</epage><pages>1633-1637</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene ring-closing metathesis (RCM) strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36820513</pmid><doi>10.1021/acs.orglett.3c00106</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-1465-2782</orcidid><orcidid>https://orcid.org/0000-0003-4504-7438</orcidid><orcidid>https://orcid.org/0000-0002-2078-5381</orcidid><orcidid>https://orcid.org/0000-0001-5297-4702</orcidid><orcidid>https://orcid.org/0000-0003-0589-7155</orcidid><orcidid>https://orcid.org/0000-0001-6430-1169</orcidid><orcidid>https://orcid.org/0000-0001-5688-7606</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2023-03, Vol.25 (10), p.1633-1637 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2779348753 |
| source | ACS Publications |
| title | Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T14%3A46%3A20IST&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%20the%20Macrolactone%20Cores%20of%20Maltepolides%20via%20a%20Diene%E2%80%93Ene%20Ring-Closing%20Metathesis%20Strategy&rft.jtitle=Organic%20letters&rft.au=Sit,%20Man%20Ki&rft.date=2023-03-17&rft.volume=25&rft.issue=10&rft.spage=1633&rft.epage=1637&rft.pages=1633-1637&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c00106&rft_dat=%3Cproquest_cross%3E2779348753%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=2779348753&rft_id=info:pmid/36820513&rfr_iscdi=true |