Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B

Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B

Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an -quinone methide a...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2020-10, Vol.22 (20), p.8161-8166
Hauptverfasser: Vieira de Castro, Tomás, Yahiaoui, Oussama, Peralta, Ricardo A, Fallon, Thomas, Lee, Victor, George, Jonathan H
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8166
container_issue 20
container_start_page 8161
container_title Organic letters
container_volume 22
creator Vieira de Castro, Tomás
Yahiaoui, Oussama
Peralta, Ricardo A
Fallon, Thomas
Lee, Victor
George, Jonathan H
description Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an -quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.
doi_str_mv 10.1021/acs.orglett.0c03156
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2449182232</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2449182232</sourcerecordid><originalsourceid>FETCH-LOGICAL-c305t-fd90409a8f4dc4ecdde76622979775ba5450aafb0375d80741203f8e129599da3</originalsourceid><addsrcrecordid>eNo9kF9LwzAUxYMobk4_gSB59KXzJmna5tHppsJAcPomlDRJXaRtZpIK-_ZWN_dy_3HOufBD6JLAlAAlN1KFqfMfjYlxCgoY4dkRGhNOWZIDp8eHOYMROgvhE4AMF3GKRowNAQWwMXqfWdfa1kSr8GrbxbUJNuB5J6vGBDyseBV9r2LvDX4x3zZY12FX46WN0XltZTOosew0XvzVe79Va9luXGfw7Byd1IPAXOz7BL0t5q93j8ny-eHp7naZKAY8JrUWkIKQRZ1qlRqltcmzjFKRizznleQpBynrCljOdQF5SiiwujCECi6ElmyCrne5G---ehNi2dqgTNPIzrg-lDRNBSkoZXSQsp1UeReCN3W58baVflsSKH-xlgPWco-13GMdXFf7B33VGn3w_HNkP4IWdj8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2449182232</pqid></control><display><type>article</type><title>Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B</title><source>American Chemical Society Journals</source><creator>Vieira de Castro, Tomás ; Yahiaoui, Oussama ; Peralta, Ricardo A ; Fallon, Thomas ; Lee, Victor ; George, Jonathan H</creator><creatorcontrib>Vieira de Castro, Tomás ; Yahiaoui, Oussama ; Peralta, Ricardo A ; Fallon, Thomas ; Lee, Victor ; George, Jonathan H</creatorcontrib><description>Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an -quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c03156</identifier><identifier>PMID: 33021803</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2020-10, Vol.22 (20), p.8161-8166</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-fd90409a8f4dc4ecdde76622979775ba5450aafb0375d80741203f8e129599da3</citedby><cites>FETCH-LOGICAL-c305t-fd90409a8f4dc4ecdde76622979775ba5450aafb0375d80741203f8e129599da3</cites><orcidid>0000-0002-7330-2160 ; 0000-0002-4032-6481</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2765,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33021803$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vieira de Castro, Tomás</creatorcontrib><creatorcontrib>Yahiaoui, Oussama</creatorcontrib><creatorcontrib>Peralta, Ricardo A</creatorcontrib><creatorcontrib>Fallon, Thomas</creatorcontrib><creatorcontrib>Lee, Victor</creatorcontrib><creatorcontrib>George, Jonathan H</creatorcontrib><title>Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an -quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNo9kF9LwzAUxYMobk4_gSB59KXzJmna5tHppsJAcPomlDRJXaRtZpIK-_ZWN_dy_3HOufBD6JLAlAAlN1KFqfMfjYlxCgoY4dkRGhNOWZIDp8eHOYMROgvhE4AMF3GKRowNAQWwMXqfWdfa1kSr8GrbxbUJNuB5J6vGBDyseBV9r2LvDX4x3zZY12FX46WN0XltZTOosew0XvzVe79Va9luXGfw7Byd1IPAXOz7BL0t5q93j8ny-eHp7naZKAY8JrUWkIKQRZ1qlRqltcmzjFKRizznleQpBynrCljOdQF5SiiwujCECi6ElmyCrne5G---ehNi2dqgTNPIzrg-lDRNBSkoZXSQsp1UeReCN3W58baVflsSKH-xlgPWco-13GMdXFf7B33VGn3w_HNkP4IWdj8</recordid><startdate>20201016</startdate><enddate>20201016</enddate><creator>Vieira de Castro, Tomás</creator><creator>Yahiaoui, Oussama</creator><creator>Peralta, Ricardo A</creator><creator>Fallon, Thomas</creator><creator>Lee, Victor</creator><creator>George, Jonathan H</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7330-2160</orcidid><orcidid>https://orcid.org/0000-0002-4032-6481</orcidid></search><sort><creationdate>20201016</creationdate><title>Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B</title><author>Vieira de Castro, Tomás ; Yahiaoui, Oussama ; Peralta, Ricardo A ; Fallon, Thomas ; Lee, Victor ; George, Jonathan H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-fd90409a8f4dc4ecdde76622979775ba5450aafb0375d80741203f8e129599da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vieira de Castro, Tomás</creatorcontrib><creatorcontrib>Yahiaoui, Oussama</creatorcontrib><creatorcontrib>Peralta, Ricardo A</creatorcontrib><creatorcontrib>Fallon, Thomas</creatorcontrib><creatorcontrib>Lee, Victor</creatorcontrib><creatorcontrib>George, Jonathan H</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>Vieira de Castro, Tomás</au><au>Yahiaoui, Oussama</au><au>Peralta, Ricardo A</au><au>Fallon, Thomas</au><au>Lee, Victor</au><au>George, Jonathan H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2020-10-16</date><risdate>2020</risdate><volume>22</volume><issue>20</issue><spage>8161</spage><epage>8166</epage><pages>8161-8166</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an -quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.</abstract><cop>United States</cop><pmid>33021803</pmid><doi>10.1021/acs.orglett.0c03156</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7330-2160</orcidid><orcidid>https://orcid.org/0000-0002-4032-6481</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-10, Vol.22 (20), p.8161-8166
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2449182232
source American Chemical Society Journals
title Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T08%3A27%3A15IST&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=Biomimetic%20Synthesis%20Enables%20the%20Structure%20Revision%20of%20Littordials%20E%20and%20F%20and%20Drychampone%20B&rft.jtitle=Organic%20letters&rft.au=Vieira%20de%20Castro,%20Tom%C3%A1s&rft.date=2020-10-16&rft.volume=22&rft.issue=20&rft.spage=8161&rft.epage=8166&rft.pages=8161-8166&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c03156&rft_dat=%3Cproquest_cross%3E2449182232%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=2449182232&rft_id=info:pmid/33021803&rfr_iscdi=true