Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone

The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunc...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (14), p.5519-5523
Main Authors: Pullella, Glenn A, Wdowiak, Adam P, Sykes, Melissa L, Lucantoni, Leonardo, Sukhoverkov, Kirill V, Zulfiqar, Bilal, Sobolev, Alexandre N, West, Nicholas P, Mylne, Joshua S, Avery, Vicky M, Piggott, Matthew J
Format: Article
Language:English
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-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183
cites cdi_FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183
container_end_page 5523
container_issue 14
container_start_page 5519
container_title Organic letters
container_volume 21
creator Pullella, Glenn A
Wdowiak, Adam P
Sykes, Melissa L
Lucantoni, Leonardo
Sukhoverkov, Kirill V
Zulfiqar, Bilal
Sobolev, Alexandre N
West, Nicholas P
Mylne, Joshua S
Avery, Vicky M
Piggott, Matthew J
description The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.
doi_str_mv 10.1021/acs.orglett.9b01838
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2254517612</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2254517612</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183</originalsourceid><addsrcrecordid>eNp9kMtOwzAQRS0EoqXwBUgoSzYpYydOnGVU8RIVIFHWluPYkCqNix-L_j2uGrpkNaOZe8e-B6FrDHMMBN8J6ebGfvXK-3nVAGYZO0FTTEmWlkDJ6bEvYIIunFsD4DipztEkw4SVGSmm6GVlvOiTj93gv5XrXGJ0ErukHny3Eb2wXdzWTnZtJ4bkVfhg4-DdmjZIn9R9Y7ZhkF54M6hLdKZF79TVWGfo8-F-tXhKl2-Pz4t6mYospz4lSmkARonQbQFKMyri13HRMqiwxFnFQFLWyianopQ0lw1oIkGqqmiJjjFn6PZwd2vNT1DO803npOp7MSgTHCeE5hSXBSZRmh2k0hrnrNJ8a2Muu-MY-J4ijxT5SJGPFKPrZnwgNBvVHj1_2KLg7iDYu9cm2CHm_ffkL4FugW4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2254517612</pqid></control><display><type>article</type><title>Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Pullella, Glenn A ; Wdowiak, Adam P ; Sykes, Melissa L ; Lucantoni, Leonardo ; Sukhoverkov, Kirill V ; Zulfiqar, Bilal ; Sobolev, Alexandre N ; West, Nicholas P ; Mylne, Joshua S ; Avery, Vicky M ; Piggott, Matthew J</creator><creatorcontrib>Pullella, Glenn A ; Wdowiak, Adam P ; Sykes, Melissa L ; Lucantoni, Leonardo ; Sukhoverkov, Kirill V ; Zulfiqar, Bilal ; Sobolev, Alexandre N ; West, Nicholas P ; Mylne, Joshua S ; Avery, Vicky M ; Piggott, Matthew J</creatorcontrib><description>The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.9b01838</identifier><identifier>PMID: 31287326</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2019-07, Vol.21 (14), p.5519-5523</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183</citedby><cites>FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183</cites><orcidid>0000-0002-5857-7051 ; 0000-0003-4957-6388</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31287326$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pullella, Glenn A</creatorcontrib><creatorcontrib>Wdowiak, Adam P</creatorcontrib><creatorcontrib>Sykes, Melissa L</creatorcontrib><creatorcontrib>Lucantoni, Leonardo</creatorcontrib><creatorcontrib>Sukhoverkov, Kirill V</creatorcontrib><creatorcontrib>Zulfiqar, Bilal</creatorcontrib><creatorcontrib>Sobolev, Alexandre N</creatorcontrib><creatorcontrib>West, Nicholas P</creatorcontrib><creatorcontrib>Mylne, Joshua S</creatorcontrib><creatorcontrib>Avery, Vicky M</creatorcontrib><creatorcontrib>Piggott, Matthew J</creatorcontrib><title>Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOwzAQRS0EoqXwBUgoSzYpYydOnGVU8RIVIFHWluPYkCqNix-L_j2uGrpkNaOZe8e-B6FrDHMMBN8J6ebGfvXK-3nVAGYZO0FTTEmWlkDJ6bEvYIIunFsD4DipztEkw4SVGSmm6GVlvOiTj93gv5XrXGJ0ErukHny3Eb2wXdzWTnZtJ4bkVfhg4-DdmjZIn9R9Y7ZhkF54M6hLdKZF79TVWGfo8-F-tXhKl2-Pz4t6mYospz4lSmkARonQbQFKMyri13HRMqiwxFnFQFLWyianopQ0lw1oIkGqqmiJjjFn6PZwd2vNT1DO803npOp7MSgTHCeE5hSXBSZRmh2k0hrnrNJ8a2Muu-MY-J4ijxT5SJGPFKPrZnwgNBvVHj1_2KLg7iDYu9cm2CHm_ffkL4FugW4</recordid><startdate>20190719</startdate><enddate>20190719</enddate><creator>Pullella, Glenn A</creator><creator>Wdowiak, Adam P</creator><creator>Sykes, Melissa L</creator><creator>Lucantoni, Leonardo</creator><creator>Sukhoverkov, Kirill V</creator><creator>Zulfiqar, Bilal</creator><creator>Sobolev, Alexandre N</creator><creator>West, Nicholas P</creator><creator>Mylne, Joshua S</creator><creator>Avery, Vicky M</creator><creator>Piggott, Matthew J</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5857-7051</orcidid><orcidid>https://orcid.org/0000-0003-4957-6388</orcidid></search><sort><creationdate>20190719</creationdate><title>Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone</title><author>Pullella, Glenn A ; Wdowiak, Adam P ; Sykes, Melissa L ; Lucantoni, Leonardo ; Sukhoverkov, Kirill V ; Zulfiqar, Bilal ; Sobolev, Alexandre N ; West, Nicholas P ; Mylne, Joshua S ; Avery, Vicky M ; Piggott, Matthew J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pullella, Glenn A</creatorcontrib><creatorcontrib>Wdowiak, Adam P</creatorcontrib><creatorcontrib>Sykes, Melissa L</creatorcontrib><creatorcontrib>Lucantoni, Leonardo</creatorcontrib><creatorcontrib>Sukhoverkov, Kirill V</creatorcontrib><creatorcontrib>Zulfiqar, Bilal</creatorcontrib><creatorcontrib>Sobolev, Alexandre N</creatorcontrib><creatorcontrib>West, Nicholas P</creatorcontrib><creatorcontrib>Mylne, Joshua S</creatorcontrib><creatorcontrib>Avery, Vicky M</creatorcontrib><creatorcontrib>Piggott, Matthew J</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>Pullella, Glenn A</au><au>Wdowiak, Adam P</au><au>Sykes, Melissa L</au><au>Lucantoni, Leonardo</au><au>Sukhoverkov, Kirill V</au><au>Zulfiqar, Bilal</au><au>Sobolev, Alexandre N</au><au>West, Nicholas P</au><au>Mylne, Joshua S</au><au>Avery, Vicky M</au><au>Piggott, Matthew J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2019-07-19</date><risdate>2019</risdate><volume>21</volume><issue>14</issue><spage>5519</spage><epage>5523</epage><pages>5519-5523</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The first approaches to the 10′-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31287326</pmid><doi>10.1021/acs.orglett.9b01838</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5857-7051</orcidid><orcidid>https://orcid.org/0000-0003-4957-6388</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2019-07, Vol.21 (14), p.5519-5523
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2254517612
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T13%3A10%3A49IST&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=Total%20Synthesis%20of%20the%20Antimalarial%20Ascidian%20Natural%20Product%20Albopunctatone&rft.jtitle=Organic%20letters&rft.au=Pullella,%20Glenn%20A&rft.date=2019-07-19&rft.volume=21&rft.issue=14&rft.spage=5519&rft.epage=5523&rft.pages=5519-5523&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.9b01838&rft_dat=%3Cproquest_cross%3E2254517612%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-2eef00852afd60ef85a83816d8091c13980c58dcb45a7c54cb0f2c0ce96d2f183%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2254517612&rft_id=info:pmid/31287326&rfr_iscdi=true