InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids
A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2022-11, Vol.13 (46), p.13893-13897 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 13897 |
|---|---|
| container_issue | 46 |
| container_start_page | 13893 |
| container_title | Chemical science (Cambridge) |
| container_volume | 13 |
| creator | Huo, Chen-Yu Zheng, Tian-Lu Dai, Wei-Hao Zhang, Zi-Hao Wang, Jin-Da Zhu, Dao-Yong Wang, Shao-Hua Zhang, Xiao-Ming Xu, Xue-Tao |
| description | A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time. |
| doi_str_mv | 10.1039/d2sc04229k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9710309</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2757161344</sourcerecordid><originalsourceid>FETCH-LOGICAL-p307t-b002beebb85b625d395d1717a5af19400278a62ba660c10ae5c83e10498852bb3</originalsourceid><addsrcrecordid>eNpdUE1LAzEQXUTBUnvxFwS8eFnNx2azexGk-FEoeNHzkmSnNjVN1k22sMUfb6RF0JnDfLw3D95k2SXBNwSz-ralQeOC0vrjJJtQXJC85Kw-_e0pPs9mIWxwCsYIp2KSfS3cguVaRmnHPbSo83YEB0iP2pq9jMY75FdIWpu2AUnXIhNT7Tpr9AE2DsU1oOiTBgqjS0Mw4ecqwA4ckspAlA7yOHaAWhOh78B504aL7GwlbYDZsU6zt8eH1_lzvnx5Wszvl3nHsIi5wpgqAKUqrkrKW1bzlggiJJcrUhcJFZUsqZJliTXBEriuGBBc1FXFqVJsmt0ddLtBbaHV4GIvbdP1Ziv7sfHSNH8RZ9bNu981tUiPxXUSuD4K9P5zgBCbrQkarE22_BAaKrggJWFFkahX_6gbP_Qu2UusglDBSMpvjSyGqQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2741273131</pqid></control><display><type>article</type><title>InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids</title><source>PubMed Central Free</source><source>DOAJ Directory of Open Access Journals</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central Open Access</source><creator>Huo, Chen-Yu ; Zheng, Tian-Lu ; Dai, Wei-Hao ; Zhang, Zi-Hao ; Wang, Jin-Da ; Zhu, Dao-Yong ; Wang, Shao-Hua ; Zhang, Xiao-Ming ; Xu, Xue-Tao</creator><creatorcontrib>Huo, Chen-Yu ; Zheng, Tian-Lu ; Dai, Wei-Hao ; Zhang, Zi-Hao ; Wang, Jin-Da ; Zhu, Dao-Yong ; Wang, Shao-Hua ; Zhang, Xiao-Ming ; Xu, Xue-Tao</creatorcontrib><description>A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d2sc04229k</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chemistry ; Substrates ; Synthesis</subject><ispartof>Chemical science (Cambridge), 2022-11, Vol.13 (46), p.13893-13897</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><rights>This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9710309/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9710309/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids></links><search><creatorcontrib>Huo, Chen-Yu</creatorcontrib><creatorcontrib>Zheng, Tian-Lu</creatorcontrib><creatorcontrib>Dai, Wei-Hao</creatorcontrib><creatorcontrib>Zhang, Zi-Hao</creatorcontrib><creatorcontrib>Wang, Jin-Da</creatorcontrib><creatorcontrib>Zhu, Dao-Yong</creatorcontrib><creatorcontrib>Wang, Shao-Hua</creatorcontrib><creatorcontrib>Zhang, Xiao-Ming</creatorcontrib><creatorcontrib>Xu, Xue-Tao</creatorcontrib><title>InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids</title><title>Chemical science (Cambridge)</title><description>A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time.</description><subject>Chemistry</subject><subject>Substrates</subject><subject>Synthesis</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdUE1LAzEQXUTBUnvxFwS8eFnNx2azexGk-FEoeNHzkmSnNjVN1k22sMUfb6RF0JnDfLw3D95k2SXBNwSz-ralQeOC0vrjJJtQXJC85Kw-_e0pPs9mIWxwCsYIp2KSfS3cguVaRmnHPbSo83YEB0iP2pq9jMY75FdIWpu2AUnXIhNT7Tpr9AE2DsU1oOiTBgqjS0Mw4ecqwA4ckspAlA7yOHaAWhOh78B504aL7GwlbYDZsU6zt8eH1_lzvnx5Wszvl3nHsIi5wpgqAKUqrkrKW1bzlggiJJcrUhcJFZUsqZJliTXBEriuGBBc1FXFqVJsmt0ddLtBbaHV4GIvbdP1Ziv7sfHSNH8RZ9bNu981tUiPxXUSuD4K9P5zgBCbrQkarE22_BAaKrggJWFFkahX_6gbP_Qu2UusglDBSMpvjSyGqQ</recordid><startdate>20221130</startdate><enddate>20221130</enddate><creator>Huo, Chen-Yu</creator><creator>Zheng, Tian-Lu</creator><creator>Dai, Wei-Hao</creator><creator>Zhang, Zi-Hao</creator><creator>Wang, Jin-Da</creator><creator>Zhu, Dao-Yong</creator><creator>Wang, Shao-Hua</creator><creator>Zhang, Xiao-Ming</creator><creator>Xu, Xue-Tao</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20221130</creationdate><title>InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids</title><author>Huo, Chen-Yu ; Zheng, Tian-Lu ; Dai, Wei-Hao ; Zhang, Zi-Hao ; Wang, Jin-Da ; Zhu, Dao-Yong ; Wang, Shao-Hua ; Zhang, Xiao-Ming ; Xu, Xue-Tao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p307t-b002beebb85b625d395d1717a5af19400278a62ba660c10ae5c83e10498852bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chemistry</topic><topic>Substrates</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huo, Chen-Yu</creatorcontrib><creatorcontrib>Zheng, Tian-Lu</creatorcontrib><creatorcontrib>Dai, Wei-Hao</creatorcontrib><creatorcontrib>Zhang, Zi-Hao</creatorcontrib><creatorcontrib>Wang, Jin-Da</creatorcontrib><creatorcontrib>Zhu, Dao-Yong</creatorcontrib><creatorcontrib>Wang, Shao-Hua</creatorcontrib><creatorcontrib>Zhang, Xiao-Ming</creatorcontrib><creatorcontrib>Xu, Xue-Tao</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huo, Chen-Yu</au><au>Zheng, Tian-Lu</au><au>Dai, Wei-Hao</au><au>Zhang, Zi-Hao</au><au>Wang, Jin-Da</au><au>Zhu, Dao-Yong</au><au>Wang, Shao-Hua</au><au>Zhang, Xiao-Ming</au><au>Xu, Xue-Tao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2022-11-30</date><risdate>2022</risdate><volume>13</volume><issue>46</issue><spage>13893</spage><epage>13897</epage><pages>13893-13897</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2sc04229k</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2022-11, Vol.13 (46), p.13893-13897 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9710309 |
| source | PubMed Central Free; DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central Open Access |
| subjects | Chemistry Substrates Synthesis |
| title | InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T14%3A04%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=InI3-catalyzed%20polyene%20cyclization%20of%20allenes%20and%20its%20application%20in%20the%20total%20synthesis%20of%20seven%20abietane-type%20diterpenoids&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Huo,%20Chen-Yu&rft.date=2022-11-30&rft.volume=13&rft.issue=46&rft.spage=13893&rft.epage=13897&rft.pages=13893-13897&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/d2sc04229k&rft_dat=%3Cproquest_pubme%3E2757161344%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2741273131&rft_id=info:pmid/&rfr_iscdi=true |