Total Synthesis of Phenanthroviridin Aglycon and Its Analog
We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodides, which were prepared from 3,5‐dimethylphenol, gave aryl‐1,4‐naphthoquinones. Treatment of the resulti...
Gespeichert in:
| Veröffentlicht in: | Asian journal of organic chemistry 2021-05, Vol.10 (5), p.1094-1096 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1096 |
|---|---|
| container_issue | 5 |
| container_start_page | 1094 |
| container_title | Asian journal of organic chemistry |
| container_volume | 10 |
| creator | Akagi, Yusuke Harasawa, Kohei Komatsu, Toshiya |
| description | We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodides, which were prepared from 3,5‐dimethylphenol, gave aryl‐1,4‐naphthoquinones. Treatment of the resulting aryl‐1,4‐naphthoquinones with aqueous ammonia, followed by oxidative cyclization and deprotection, successfully yielded phenanthroviridin aglycon (1,8‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione) and its analog (1,11‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione).
Phenanthroviridin aglycon, which has an ary‐1,4‐naphthoquinone skeleton, exhibits interesting antibacterial and anticancer activities. In this paper, we describe the total synthesis of phenanthroviridin aglycon and its analog utilizing the Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodide. |
| doi_str_mv | 10.1002/ajoc.202100142 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2526608432</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2526608432</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3832-326fd761ebe23074594bf25c5ef562c35c75c6993b22f4b35c80306252dc27e3</originalsourceid><addsrcrecordid>eNqFkN1LwzAUxYMoOOZefQ743JncNE2LT2X4MRlMsO8hTZOtozYz6ZT-92ZM5qP35d4Dv3M5HIRuKZlTQuBe7ZyeA4EoaAoXaAK0YAnPKb8830Rco1kIOxJHiIJCMUEPlRtUh9_Hftia0AbsLH7bml5F7d1X69um7XG56Ubteqz6Bi-HgMtedW5zg66s6oKZ_e4pqp4eq8VLslo_LxflKtEsZ5AwyGwjMmpqA4yIlBdpbYFrbizPQDOuBddZUbAawKZ11DlhJAMOjQZh2BTdnd7uvfs8mDDInTv4mCDIyGQZyVMGkZqfKO1dCN5Yuffth_KjpEQeK5LHiuS5omgoTobvtjPjP7QsX9eLP-8PeKhoUA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2526608432</pqid></control><display><type>article</type><title>Total Synthesis of Phenanthroviridin Aglycon and Its Analog</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Akagi, Yusuke ; Harasawa, Kohei ; Komatsu, Toshiya</creator><creatorcontrib>Akagi, Yusuke ; Harasawa, Kohei ; Komatsu, Toshiya</creatorcontrib><description>We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodides, which were prepared from 3,5‐dimethylphenol, gave aryl‐1,4‐naphthoquinones. Treatment of the resulting aryl‐1,4‐naphthoquinones with aqueous ammonia, followed by oxidative cyclization and deprotection, successfully yielded phenanthroviridin aglycon (1,8‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione) and its analog (1,11‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione).
Phenanthroviridin aglycon, which has an ary‐1,4‐naphthoquinone skeleton, exhibits interesting antibacterial and anticancer activities. In this paper, we describe the total synthesis of phenanthroviridin aglycon and its analog utilizing the Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodide.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202100142</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>aglycon ; Ammonia ; Anticancer properties ; Aromatic compounds ; arylation ; Iodides ; Organic chemistry ; palladium ; phenanthroviridin ; quinones ; Synthesis</subject><ispartof>Asian journal of organic chemistry, 2021-05, Vol.10 (5), p.1094-1096</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3832-326fd761ebe23074594bf25c5ef562c35c75c6993b22f4b35c80306252dc27e3</citedby><cites>FETCH-LOGICAL-c3832-326fd761ebe23074594bf25c5ef562c35c75c6993b22f4b35c80306252dc27e3</cites><orcidid>0000-0002-4303-8733</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.202100142$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202100142$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Akagi, Yusuke</creatorcontrib><creatorcontrib>Harasawa, Kohei</creatorcontrib><creatorcontrib>Komatsu, Toshiya</creatorcontrib><title>Total Synthesis of Phenanthroviridin Aglycon and Its Analog</title><title>Asian journal of organic chemistry</title><description>We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodides, which were prepared from 3,5‐dimethylphenol, gave aryl‐1,4‐naphthoquinones. Treatment of the resulting aryl‐1,4‐naphthoquinones with aqueous ammonia, followed by oxidative cyclization and deprotection, successfully yielded phenanthroviridin aglycon (1,8‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione) and its analog (1,11‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione).
Phenanthroviridin aglycon, which has an ary‐1,4‐naphthoquinone skeleton, exhibits interesting antibacterial and anticancer activities. In this paper, we describe the total synthesis of phenanthroviridin aglycon and its analog utilizing the Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodide.</description><subject>aglycon</subject><subject>Ammonia</subject><subject>Anticancer properties</subject><subject>Aromatic compounds</subject><subject>arylation</subject><subject>Iodides</subject><subject>Organic chemistry</subject><subject>palladium</subject><subject>phenanthroviridin</subject><subject>quinones</subject><subject>Synthesis</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkN1LwzAUxYMoOOZefQ743JncNE2LT2X4MRlMsO8hTZOtozYz6ZT-92ZM5qP35d4Dv3M5HIRuKZlTQuBe7ZyeA4EoaAoXaAK0YAnPKb8830Rco1kIOxJHiIJCMUEPlRtUh9_Hftia0AbsLH7bml5F7d1X69um7XG56Ubteqz6Bi-HgMtedW5zg66s6oKZ_e4pqp4eq8VLslo_LxflKtEsZ5AwyGwjMmpqA4yIlBdpbYFrbizPQDOuBddZUbAawKZ11DlhJAMOjQZh2BTdnd7uvfs8mDDInTv4mCDIyGQZyVMGkZqfKO1dCN5Yuffth_KjpEQeK5LHiuS5omgoTobvtjPjP7QsX9eLP-8PeKhoUA</recordid><startdate>202105</startdate><enddate>202105</enddate><creator>Akagi, Yusuke</creator><creator>Harasawa, Kohei</creator><creator>Komatsu, Toshiya</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-4303-8733</orcidid></search><sort><creationdate>202105</creationdate><title>Total Synthesis of Phenanthroviridin Aglycon and Its Analog</title><author>Akagi, Yusuke ; Harasawa, Kohei ; Komatsu, Toshiya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3832-326fd761ebe23074594bf25c5ef562c35c75c6993b22f4b35c80306252dc27e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>aglycon</topic><topic>Ammonia</topic><topic>Anticancer properties</topic><topic>Aromatic compounds</topic><topic>arylation</topic><topic>Iodides</topic><topic>Organic chemistry</topic><topic>palladium</topic><topic>phenanthroviridin</topic><topic>quinones</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Akagi, Yusuke</creatorcontrib><creatorcontrib>Harasawa, Kohei</creatorcontrib><creatorcontrib>Komatsu, Toshiya</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Akagi, Yusuke</au><au>Harasawa, Kohei</au><au>Komatsu, Toshiya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Phenanthroviridin Aglycon and Its Analog</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2021-05</date><risdate>2021</risdate><volume>10</volume><issue>5</issue><spage>1094</spage><epage>1096</epage><pages>1094-1096</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodides, which were prepared from 3,5‐dimethylphenol, gave aryl‐1,4‐naphthoquinones. Treatment of the resulting aryl‐1,4‐naphthoquinones with aqueous ammonia, followed by oxidative cyclization and deprotection, successfully yielded phenanthroviridin aglycon (1,8‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione) and its analog (1,11‐dihydroxy‐3‐methylbenzo[b]phenanthridine‐7,12‐dione).
Phenanthroviridin aglycon, which has an ary‐1,4‐naphthoquinone skeleton, exhibits interesting antibacterial and anticancer activities. In this paper, we describe the total synthesis of phenanthroviridin aglycon and its analog utilizing the Pd‐catalyzed direct arylation of 5‐hydroxy‐1,4‐naphthoquinone with aryl iodide.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202100142</doi><tpages>3</tpages><orcidid>https://orcid.org/0000-0002-4303-8733</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2193-5807 |
| ispartof | Asian journal of organic chemistry, 2021-05, Vol.10 (5), p.1094-1096 |
| issn | 2193-5807 2193-5815 |
| language | eng |
| recordid | cdi_proquest_journals_2526608432 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | aglycon Ammonia Anticancer properties Aromatic compounds arylation Iodides Organic chemistry palladium phenanthroviridin quinones Synthesis |
| title | Total Synthesis of Phenanthroviridin Aglycon and Its Analog |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T03%3A20%3A40IST&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%20Phenanthroviridin%20Aglycon%20and%20Its%20Analog&rft.jtitle=Asian%20journal%20of%20organic%20chemistry&rft.au=Akagi,%20Yusuke&rft.date=2021-05&rft.volume=10&rft.issue=5&rft.spage=1094&rft.epage=1096&rft.pages=1094-1096&rft.issn=2193-5807&rft.eissn=2193-5815&rft_id=info:doi/10.1002/ajoc.202100142&rft_dat=%3Cproquest_cross%3E2526608432%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=2526608432&rft_id=info:pmid/&rfr_iscdi=true |