Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues

Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane di...

Full description

Saved in:
Bibliographic Details
Published in:MolBank 2000-04, Vol.5 (4), p.674-698
Main Author: Dragojlovic, Veljko
Format: Article
Language:English
Subjects:
Acids
bifunctional reagents
methylenecyclopentane annulation
Natural products
Potassium
Reagents
sesquiterpenoid synthesis
Subergorgic acid
Toxicity
triquinane synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213
cites cdi_FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213
container_end_page 698
container_issue 4
container_start_page 674
container_title MolBank
container_volume 5
creator Dragojlovic, Veljko
description Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.
doi_str_mv 10.3390/50400674
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_f57361e52d02456ca285e4ea056f8e77</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_f57361e52d02456ca285e4ea056f8e77</doaj_id><sourcerecordid>3321781121</sourcerecordid><originalsourceid>FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213</originalsourceid><addsrcrecordid>eNqFkU9LAzEQxRdRsFbBjxDw4qU6-beb9VbE2kLBQ9dzyCbZNmXdtMkuWj-9W6uiJ2FghuHNj3m8JLnEcENpDrccGECasaNkgBmBEQWWH_-aT5OzGNcABDPMB8nbYte0KxtdRL5CCk3dclXv0KRrdOt8o2r3bg0qgtt2rlGNvUOLtjPORlT4VxVM7G8K36oa_QEtutKGpQ9Lp9FYO4NUY9CsjWjcI_2ys_E8OalUHe3FVx8mz5OH4n46mj89zu7H85GmArcjgvMMBC0xo5xUXOdGl0ZBhrmhZUrFvpQ1eSY0UCZSkplS2ZwII6wgBNNhMjtwjVdruQnuRYWd9MrJz0X_olShdbq2suIZTbHlxABhPNWKCG6ZVcDTStgs61lXB9Ym-G3voZVr34XeUZSYUww5J2n-jwoY7jVpr7o-qHTwMQZb_fyGQe6TlN9J0g-X342-</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1530416936</pqid></control><display><type>article</type><title>Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues</title><source>Publicly Available Content Database</source><creator>Dragojlovic, Veljko</creator><creatorcontrib>Dragojlovic, Veljko</creatorcontrib><description>Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>EISSN: 1422-8599</identifier><identifier>DOI: 10.3390/50400674</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>Acids ; bifunctional reagents ; methylenecyclopentane annulation ; Natural products ; Potassium ; Reagents ; sesquiterpenoid synthesis ; Subergorgic acid ; Toxicity ; triquinane synthesis</subject><ispartof>MolBank, 2000-04, Vol.5 (4), p.674-698</ispartof><rights>Copyright MDPI AG 2000</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213</citedby><cites>FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1530416936/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1530416936?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,25732,27903,27904,36991,44569,74872</link.rule.ids></links><search><creatorcontrib>Dragojlovic, Veljko</creatorcontrib><title>Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues</title><title>MolBank</title><description>Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.</description><subject>Acids</subject><subject>bifunctional reagents</subject><subject>methylenecyclopentane annulation</subject><subject>Natural products</subject><subject>Potassium</subject><subject>Reagents</subject><subject>sesquiterpenoid synthesis</subject><subject>Subergorgic acid</subject><subject>Toxicity</subject><subject>triquinane synthesis</subject><issn>1420-3049</issn><issn>1420-3049</issn><issn>1422-8599</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNqFkU9LAzEQxRdRsFbBjxDw4qU6-beb9VbE2kLBQ9dzyCbZNmXdtMkuWj-9W6uiJ2FghuHNj3m8JLnEcENpDrccGECasaNkgBmBEQWWH_-aT5OzGNcABDPMB8nbYte0KxtdRL5CCk3dclXv0KRrdOt8o2r3bg0qgtt2rlGNvUOLtjPORlT4VxVM7G8K36oa_QEtutKGpQ9Lp9FYO4NUY9CsjWjcI_2ys_E8OalUHe3FVx8mz5OH4n46mj89zu7H85GmArcjgvMMBC0xo5xUXOdGl0ZBhrmhZUrFvpQ1eSY0UCZSkplS2ZwII6wgBNNhMjtwjVdruQnuRYWd9MrJz0X_olShdbq2suIZTbHlxABhPNWKCG6ZVcDTStgs61lXB9Ym-G3voZVr34XeUZSYUww5J2n-jwoY7jVpr7o-qHTwMQZb_fyGQe6TlN9J0g-X342-</recordid><startdate>20000401</startdate><enddate>20000401</enddate><creator>Dragojlovic, Veljko</creator><general>MDPI AG</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>L7M</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>DOA</scope></search><sort><creationdate>20000401</creationdate><title>Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues</title><author>Dragojlovic, Veljko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Acids</topic><topic>bifunctional reagents</topic><topic>methylenecyclopentane annulation</topic><topic>Natural products</topic><topic>Potassium</topic><topic>Reagents</topic><topic>sesquiterpenoid synthesis</topic><topic>Subergorgic acid</topic><topic>Toxicity</topic><topic>triquinane synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dragojlovic, Veljko</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science &amp; Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Materials science collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health &amp; Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Open Access: DOAJ - Directory of Open Access Journals</collection><jtitle>MolBank</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dragojlovic, Veljko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues</atitle><jtitle>MolBank</jtitle><date>2000-04-01</date><risdate>2000</risdate><volume>5</volume><issue>4</issue><spage>674</spage><epage>698</epage><pages>674-698</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><eissn>1422-8599</eissn><abstract>Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.</abstract><cop>Basel</cop><pub>MDPI AG</pub><doi>10.3390/50400674</doi><tpages>25</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1420-3049
ispartof MolBank, 2000-04, Vol.5 (4), p.674-698
issn 1420-3049
1420-3049
1422-8599
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_f57361e52d02456ca285e4ea056f8e77
source Publicly Available Content Database
subjects Acids
bifunctional reagents
methylenecyclopentane annulation
Natural products
Potassium
Reagents
sesquiterpenoid synthesis
Subergorgic acid
Toxicity
triquinane synthesis
title Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T06%3A42%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20a%20Highly%20Functionalized%20Triquinane:%20Studies%20Towards%20a%20Total%20Synthesis%20of%20Subergorgic%20Acid%20and%20Its%20Analogues&rft.jtitle=MolBank&rft.au=Dragojlovic,%20Veljko&rft.date=2000-04-01&rft.volume=5&rft.issue=4&rft.spage=674&rft.epage=698&rft.pages=674-698&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/50400674&rft_dat=%3Cproquest_doaj_%3E3321781121%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c381t-2197083b14352f5c9dcbda0715d3b6386386aed978c0348627dbae928d8e82213%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1530416936&rft_id=info:pmid/&rfr_iscdi=true