Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate
The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinon...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1999-12, Vol.62 (12), p.1643-1645 |
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| container_end_page | 1645 |
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| container_issue | 12 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 62 |
| creator | Nunes, Ruth L Bieber, Lothar W Longo, Ricardo L |
| description | The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations. |
| doi_str_mv | 10.1021/np990277g |
| format | Article |
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Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np990277g</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; biochemical pathways ; chemical constituents of plants ; chemical reactions ; Chemistry ; Exact sciences and technology ; heartwood ; hydrolysis ; hydroquinone ; mansonia altissima ; metabolites ; Organic chemistry ; precursors ; Preparations and properties ; sesquiterpenoids ; synthesis ; Terpenoids</subject><ispartof>Journal of natural products (Washington, D.C.), 1999-12, Vol.62 (12), p.1643-1645</ispartof><rights>Copyright © 1999 American Chemical Society and American Society of Pharmacognosy</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-99bbe0ad4dcf0d8443fc2013d2376d161e48d269904cae0150187aa180fac6c73</citedby><cites>FETCH-LOGICAL-a414t-99bbe0ad4dcf0d8443fc2013d2376d161e48d269904cae0150187aa180fac6c73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np990277g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np990277g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1247562$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Nunes, Ruth L</creatorcontrib><creatorcontrib>Bieber, Lothar W</creatorcontrib><creatorcontrib>Longo, Ricardo L</creatorcontrib><title>Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>biochemical pathways</subject><subject>chemical constituents of plants</subject><subject>chemical reactions</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>heartwood</subject><subject>hydrolysis</subject><subject>hydroquinone</subject><subject>mansonia altissima</subject><subject>metabolites</subject><subject>Organic chemistry</subject><subject>precursors</subject><subject>Preparations and properties</subject><subject>sesquiterpenoids</subject><subject>synthesis</subject><subject>Terpenoids</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNptkE8vBEEQxTtCYi0Hn8AcODgM1X-me-bIskgIsUskDp3S07NmrenVPcR-e83IujhVKu_3XqoeIdsUDigwetjMiwKYUpMV0qMZg1QCy1ZJD6jkKc-lWCcbIUwBgEOR9cjjaNG0zzbUIXFVcoVNcI1rbDJMjjHYMnFNEuXk1k5qF-zMmrb-sMn5ovRutvh1Ybe_vdc_1pMajW2xtZtkrcJZsFu_s0_uhqfjwXl6eX12MTi6TFFQ0aZF8fRkAUtRmgrKXAheGQaUl4wrWVJJrchLJuNfwqAFmgHNFSLNoUIjjeJ9st_lGu9C8LbSc1-_ol9oCvq7Fb1sJbK7HTvHYHBWeWxMHf4MTKhMsoilHVaH1n4uZfQvWiquMj2-GWk1fmD3eVxuIr_T8RU6jRMfI-9G308AKwQIziOx1xFogp66d9_ESv458As1A4Yr</recordid><startdate>19991201</startdate><enddate>19991201</enddate><creator>Nunes, Ruth L</creator><creator>Bieber, Lothar W</creator><creator>Longo, Ricardo L</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19991201</creationdate><title>Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate</title><author>Nunes, Ruth L ; Bieber, Lothar W ; Longo, Ricardo L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-99bbe0ad4dcf0d8443fc2013d2376d161e48d269904cae0150187aa180fac6c73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>biochemical pathways</topic><topic>chemical constituents of plants</topic><topic>chemical reactions</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>heartwood</topic><topic>hydrolysis</topic><topic>hydroquinone</topic><topic>mansonia altissima</topic><topic>metabolites</topic><topic>Organic chemistry</topic><topic>precursors</topic><topic>Preparations and properties</topic><topic>sesquiterpenoids</topic><topic>synthesis</topic><topic>Terpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nunes, Ruth L</creatorcontrib><creatorcontrib>Bieber, Lothar W</creatorcontrib><creatorcontrib>Longo, Ricardo L</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nunes, Ruth L</au><au>Bieber, Lothar W</au><au>Longo, Ricardo L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1999-12-01</date><risdate>1999</risdate><volume>62</volume><issue>12</issue><spage>1643</spage><epage>1645</epage><pages>1643-1645</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><doi>10.1021/np990277g</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 1999-12, Vol.62 (12), p.1643-1645 |
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| source | ACS Publications |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids biochemical pathways chemical constituents of plants chemical reactions Chemistry Exact sciences and technology heartwood hydrolysis hydroquinone mansonia altissima metabolites Organic chemistry precursors Preparations and properties sesquiterpenoids synthesis Terpenoids |
| title | Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate |
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