Efforts toward the Total Synthesis of Elisabethin A
We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cycliza...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2022-11, Vol.87 (22), p.15333-15349 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 15349 |
|---|---|
| container_issue | 22 |
| container_start_page | 15333 |
| container_title | Journal of organic chemistry |
| container_volume | 87 |
| creator | Kaiser, Maximilian Schönbauer, David Schragl, Katharina Weil, Matthias Gaertner, Peter Enev, Valentin S. |
| description | We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether. |
| doi_str_mv | 10.1021/acs.joc.2c01914 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9680034</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2729029564</sourcerecordid><originalsourceid>FETCH-LOGICAL-a429t-5577d6aa4d6139682202b59ca42b5b3ab8feb265b700ac3b327fcd0b8db3af973</originalsourceid><addsrcrecordid>eNp1kM1LwzAYh4Mobk7P3qRHQbq9SZp-XIQx5gcMPDjPIUlT19E1M0mV_fdmdA49mEsIv-f9veFB6BrDGAPBE6HceG3UmCjABU5O0BAzAnFaQHKKhgCExJSkdIAunFtDOIyxczSgKckpUDxEdF5VxnoXefMlbBn5lY6Wxosmet214eFqF5kqmje1E1L7Vd1G00t0VonG6avDPUJvD_Pl7ClevDw-z6aLWCSk8DFjWVamQiRlimmR5oQAkaxQIZVMUiHzSkuSMpkBCEUlJVmlSpB5GcKqyOgI3fe9205udKl0661o-NbWG2F33Iia_03aesXfzScPywBoEgpuDwXWfHTaeb6pndJNI1ptOsdJRgogBUv36KRHlTXOWV0d12Dge9U8qOZBNT-oDhM3v3935H_cBuCuB_rJzrZB1r913414idM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2729029564</pqid></control><display><type>article</type><title>Efforts toward the Total Synthesis of Elisabethin A</title><source>MEDLINE</source><source>American Chemical Society Publications</source><creator>Kaiser, Maximilian ; Schönbauer, David ; Schragl, Katharina ; Weil, Matthias ; Gaertner, Peter ; Enev, Valentin S.</creator><creatorcontrib>Kaiser, Maximilian ; Schönbauer, David ; Schragl, Katharina ; Weil, Matthias ; Gaertner, Peter ; Enev, Valentin S.</creatorcontrib><description>We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c01914</identifier><identifier>PMID: 36283031</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cyclization ; Diterpenes ; Spiro Compounds ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2022-11, Vol.87 (22), p.15333-15349</ispartof><rights>2022 The Authors. Published by American Chemical Society</rights><rights>2022 The Authors. Published by American Chemical Society 2022 The Authors</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a429t-5577d6aa4d6139682202b59ca42b5b3ab8feb265b700ac3b327fcd0b8db3af973</citedby><cites>FETCH-LOGICAL-a429t-5577d6aa4d6139682202b59ca42b5b3ab8feb265b700ac3b327fcd0b8db3af973</cites><orcidid>0000-0001-5235-9910 ; 0000-0001-7559-0787 ; 0000-0002-2097-385X</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.joc.2c01914$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01914$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36283031$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaiser, Maximilian</creatorcontrib><creatorcontrib>Schönbauer, David</creatorcontrib><creatorcontrib>Schragl, Katharina</creatorcontrib><creatorcontrib>Weil, Matthias</creatorcontrib><creatorcontrib>Gaertner, Peter</creatorcontrib><creatorcontrib>Enev, Valentin S.</creatorcontrib><title>Efforts toward the Total Synthesis of Elisabethin A</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether.</description><subject>Cyclization</subject><subject>Diterpenes</subject><subject>Spiro Compounds</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kM1LwzAYh4Mobk7P3qRHQbq9SZp-XIQx5gcMPDjPIUlT19E1M0mV_fdmdA49mEsIv-f9veFB6BrDGAPBE6HceG3UmCjABU5O0BAzAnFaQHKKhgCExJSkdIAunFtDOIyxczSgKckpUDxEdF5VxnoXefMlbBn5lY6Wxosmet214eFqF5kqmje1E1L7Vd1G00t0VonG6avDPUJvD_Pl7ClevDw-z6aLWCSk8DFjWVamQiRlimmR5oQAkaxQIZVMUiHzSkuSMpkBCEUlJVmlSpB5GcKqyOgI3fe9205udKl0661o-NbWG2F33Iia_03aesXfzScPywBoEgpuDwXWfHTaeb6pndJNI1ptOsdJRgogBUv36KRHlTXOWV0d12Dge9U8qOZBNT-oDhM3v3935H_cBuCuB_rJzrZB1r913414idM</recordid><startdate>20221118</startdate><enddate>20221118</enddate><creator>Kaiser, Maximilian</creator><creator>Schönbauer, David</creator><creator>Schragl, Katharina</creator><creator>Weil, Matthias</creator><creator>Gaertner, Peter</creator><creator>Enev, Valentin S.</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><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-5235-9910</orcidid><orcidid>https://orcid.org/0000-0001-7559-0787</orcidid><orcidid>https://orcid.org/0000-0002-2097-385X</orcidid></search><sort><creationdate>20221118</creationdate><title>Efforts toward the Total Synthesis of Elisabethin A</title><author>Kaiser, Maximilian ; Schönbauer, David ; Schragl, Katharina ; Weil, Matthias ; Gaertner, Peter ; Enev, Valentin S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a429t-5577d6aa4d6139682202b59ca42b5b3ab8feb265b700ac3b327fcd0b8db3af973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Cyclization</topic><topic>Diterpenes</topic><topic>Spiro Compounds</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaiser, Maximilian</creatorcontrib><creatorcontrib>Schönbauer, David</creatorcontrib><creatorcontrib>Schragl, Katharina</creatorcontrib><creatorcontrib>Weil, Matthias</creatorcontrib><creatorcontrib>Gaertner, Peter</creatorcontrib><creatorcontrib>Enev, Valentin S.</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaiser, Maximilian</au><au>Schönbauer, David</au><au>Schragl, Katharina</au><au>Weil, Matthias</au><au>Gaertner, Peter</au><au>Enev, Valentin S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efforts toward the Total Synthesis of Elisabethin A</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2022-11-18</date><risdate>2022</risdate><volume>87</volume><issue>22</issue><spage>15333</spage><epage>15349</epage><pages>15333-15349</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36283031</pmid><doi>10.1021/acs.joc.2c01914</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-5235-9910</orcidid><orcidid>https://orcid.org/0000-0001-7559-0787</orcidid><orcidid>https://orcid.org/0000-0002-2097-385X</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2022-11, Vol.87 (22), p.15333-15349 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9680034 |
| source | MEDLINE; American Chemical Society Publications |
| subjects | Cyclization Diterpenes Spiro Compounds Stereoisomerism |
| title | Efforts toward the Total Synthesis of Elisabethin A |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T17%3A39%3A37IST&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=Efforts%20toward%20the%20Total%20Synthesis%20of%20Elisabethin%20A&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Kaiser,%20Maximilian&rft.date=2022-11-18&rft.volume=87&rft.issue=22&rft.spage=15333&rft.epage=15349&rft.pages=15333-15349&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.2c01914&rft_dat=%3Cproquest_pubme%3E2729029564%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=2729029564&rft_id=info:pmid/36283031&rfr_iscdi=true |