Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction
Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite e...
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| Veröffentlicht in: | Chemical science (Cambridge) 2024-07, Vol.15 (27), p.1541-1546 |
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| container_title | Chemical science (Cambridge) |
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| creator | Andringa, Ruben L. H Marinus, Nittert Bunt, Daan V Haiderer, Elizabeth R Abramovitch, Robert B Brown, Christopher D Rhee, Kyu Y Witte, Martin D Minnaard, Adriaan J |
| description | Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared
via
site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell
Mycobacterium tuberculosis
and does not inhibit growth of the bacterium.
The densely functionalized terpene glycoside dissectol A has been prepared
via
site-selective oxidation and an intramolecular Tsuji-Trost allylic alkylation reaction with an enediolate as the nucleophile. |
| doi_str_mv | 10.1039/d4sc01745e |
| format | Article |
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via
site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell
Mycobacterium tuberculosis
and does not inhibit growth of the bacterium.
The densely functionalized terpene glycoside dissectol A has been prepared
via
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via
site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell
Mycobacterium tuberculosis
and does not inhibit growth of the bacterium.
The densely functionalized terpene glycoside dissectol A has been prepared
via
site-selective oxidation and an intramolecular Tsuji-Trost allylic alkylation reaction with an enediolate as the nucleophile.</description><subject>Alkylation</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Flowering</subject><subject>Nucleophiles</subject><subject>Oxidation</subject><subject>Plants (botany)</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkc1rFEEQxRtRTEhy8a40eJHgaH_NzvQphDUmQtCD67mp6alJepntjl09Qv57Z7NxjdalCurH41U9xl5J8UEKbT_2hryQjanxGTtUwshqUWv7fD8rccBOiNZiLq1lrZqX7EC31hqj9CH7ukoFRk73sdwiBeJp4H0gQl_SyM_f84lCvOEQOUbsQxqhYNUBYc9XNK1DtcqJCs8IvoQUj9mLAUbCk8d-xH58vlgtr6rrb5dflufXldeyLVVrEfQCTQ3QqaZGEAutjNBSN53wtRCDx3oQaDoNEvrWt32rlO66QTU4gNJH7Gynezd1G-w9xpJhdHc5bCDfuwTB_buJ4dbdpF9OSqVN28pZ4d2jQk4_J6TiNoE8jiNETBM5LRorm1pYMaNv_0PXacpxvm9LNQtrrdxaOt1Rfv4IZRz2bqRw26jcJ_N9-RDVxQy_eep_j_4JZgZe74BMfr_9m7X-DS7hmKg</recordid><startdate>20240710</startdate><enddate>20240710</enddate><creator>Andringa, Ruben L. H</creator><creator>Marinus, Nittert</creator><creator>Bunt, Daan V</creator><creator>Haiderer, Elizabeth R</creator><creator>Abramovitch, Robert B</creator><creator>Brown, Christopher D</creator><creator>Rhee, Kyu Y</creator><creator>Witte, Martin D</creator><creator>Minnaard, Adriaan J</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2182-8133</orcidid><orcidid>https://orcid.org/0000-0003-4660-2974</orcidid><orcidid>https://orcid.org/0000-0002-5966-1300</orcidid></search><sort><creationdate>20240710</creationdate><title>Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction</title><author>Andringa, Ruben L. H ; Marinus, Nittert ; Bunt, Daan V ; Haiderer, Elizabeth R ; Abramovitch, Robert B ; Brown, Christopher D ; Rhee, Kyu Y ; Witte, Martin D ; Minnaard, Adriaan J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c318t-89ea36e45aab275ea0632403137b0c500fce5f0e4b3a1ad8c8d8223bbf27efa23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkylation</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Flowering</topic><topic>Nucleophiles</topic><topic>Oxidation</topic><topic>Plants (botany)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Andringa, Ruben L. H</creatorcontrib><creatorcontrib>Marinus, Nittert</creatorcontrib><creatorcontrib>Bunt, Daan V</creatorcontrib><creatorcontrib>Haiderer, Elizabeth R</creatorcontrib><creatorcontrib>Abramovitch, Robert B</creatorcontrib><creatorcontrib>Brown, Christopher D</creatorcontrib><creatorcontrib>Rhee, Kyu Y</creatorcontrib><creatorcontrib>Witte, Martin D</creatorcontrib><creatorcontrib>Minnaard, Adriaan J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><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>Andringa, Ruben L. H</au><au>Marinus, Nittert</au><au>Bunt, Daan V</au><au>Haiderer, Elizabeth R</au><au>Abramovitch, Robert B</au><au>Brown, Christopher D</au><au>Rhee, Kyu Y</au><au>Witte, Martin D</au><au>Minnaard, Adriaan J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2024-07-10</date><risdate>2024</risdate><volume>15</volume><issue>27</issue><spage>1541</spage><epage>1546</epage><pages>1541-1546</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared
via
site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell
Mycobacterium tuberculosis
and does not inhibit growth of the bacterium.
The densely functionalized terpene glycoside dissectol A has been prepared
via
site-selective oxidation and an intramolecular Tsuji-Trost allylic alkylation reaction with an enediolate as the nucleophile.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38994423</pmid><doi>10.1039/d4sc01745e</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2182-8133</orcidid><orcidid>https://orcid.org/0000-0003-4660-2974</orcidid><orcidid>https://orcid.org/0000-0002-5966-1300</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Alkylation Chemical synthesis Chemistry Flowering Nucleophiles Oxidation Plants (botany) |
| title | Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction |
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