A revised structure for aubergenone, a sesquiterpenoid related to eudesmane: synthesis of 4-epi-aubergenone
Syntheses of 4-epi-aubergenone, a sesquiterpenoid related to eudesmane, are described. One synthesis afforded this sesquiterpenoid as a racemate ( 12 ) whereas another, utilizing (+)-carissone as starting material, afforded an enantiomer ( 12 a). The fact that naturally occurring aubergenone is the...
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| Veröffentlicht in: | Canadian journal of chemistry 1978-10, Vol.56 (19), p.2508-2512 |
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| container_title | Canadian journal of chemistry |
| container_volume | 56 |
| creator | Kelly, Ronald B Alward, Sandra J Murty, K. Suryanarayana Stothers, J. B |
| description | Syntheses of 4-epi-aubergenone, a sesquiterpenoid related to eudesmane, are described. One synthesis afforded this sesquiterpenoid as a racemate (
12
) whereas another, utilizing (+)-carissone as starting material, afforded an enantiomer (
12
a). The fact that naturally occurring aubergenone is the C(4) epimer of the thermodynamically more stable synthetic
12
was revealed by the discovery that it was completely converted into the latter by treatment with base. This epimeric relationship is substantiated by comparison of the nmr spectra of the two isomers. Evidence requiring the reformulation of the structure of aubergenone as
13
is adduced. |
| doi_str_mv | 10.1139/v78-411 |
| format | Article |
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12
) whereas another, utilizing (+)-carissone as starting material, afforded an enantiomer (
12
a). The fact that naturally occurring aubergenone is the C(4) epimer of the thermodynamically more stable synthetic
12
was revealed by the discovery that it was completely converted into the latter by treatment with base. This epimeric relationship is substantiated by comparison of the nmr spectra of the two isomers. Evidence requiring the reformulation of the structure of aubergenone as
13
is adduced.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v78-411</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1978-10, Vol.56 (19), p.2508-2512</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-7fd63b516336546c57d9593c5ca43b5c5c44968ff859d94abb7430d405dfd8633</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v78-411$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v78-411$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids></links><search><creatorcontrib>Kelly, Ronald B</creatorcontrib><creatorcontrib>Alward, Sandra J</creatorcontrib><creatorcontrib>Murty, K. Suryanarayana</creatorcontrib><creatorcontrib>Stothers, J. B</creatorcontrib><title>A revised structure for aubergenone, a sesquiterpenoid related to eudesmane: synthesis of 4-epi-aubergenone</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Syntheses of 4-epi-aubergenone, a sesquiterpenoid related to eudesmane, are described. One synthesis afforded this sesquiterpenoid as a racemate (
12
) whereas another, utilizing (+)-carissone as starting material, afforded an enantiomer (
12
a). The fact that naturally occurring aubergenone is the C(4) epimer of the thermodynamically more stable synthetic
12
was revealed by the discovery that it was completely converted into the latter by treatment with base. This epimeric relationship is substantiated by comparison of the nmr spectra of the two isomers. Evidence requiring the reformulation of the structure of aubergenone as
13
is adduced.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><recordid>eNp9kD1PwzAYhC0EEqUg_oInkBABO7aTmK2q-JIqscAcOfZrGmiT4Nep1H-PUTuwwHS603M3HCHnnN1wLvTtpqwyyfkBmXBZsUzkmh-SCWMsxUzmx-QE8SPZkuVqQj5nNMCmRXAUYxhtHANQ3wdqxgbCO3R9B9fUUAT8GtsIYUhR61JpZWIqxZ7C6ADXpoM7itsuLgFbpL2nMoOhzX7tnJIjb1YIZ3udkreH-9f5U7Z4eXyezxaZFUrFrPSuEI3ihRCFkoVVpdNKC6uskSlPKqUuKu8rpZ2WpmlKKZiTTDnvqtSaksvdrg09YgBfD6Fdm7CtOat_PqrTR3X6KJFXO7ILNgCCCXb5D3zxN7yH6sF58Q2QmHZQ</recordid><startdate>19781001</startdate><enddate>19781001</enddate><creator>Kelly, Ronald B</creator><creator>Alward, Sandra J</creator><creator>Murty, K. Suryanarayana</creator><creator>Stothers, J. B</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19781001</creationdate><title>A revised structure for aubergenone, a sesquiterpenoid related to eudesmane: synthesis of 4-epi-aubergenone</title><author>Kelly, Ronald B ; Alward, Sandra J ; Murty, K. Suryanarayana ; Stothers, J. B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-7fd63b516336546c57d9593c5ca43b5c5c44968ff859d94abb7430d405dfd8633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kelly, Ronald B</creatorcontrib><creatorcontrib>Alward, Sandra J</creatorcontrib><creatorcontrib>Murty, K. Suryanarayana</creatorcontrib><creatorcontrib>Stothers, J. B</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kelly, Ronald B</au><au>Alward, Sandra J</au><au>Murty, K. Suryanarayana</au><au>Stothers, J. B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A revised structure for aubergenone, a sesquiterpenoid related to eudesmane: synthesis of 4-epi-aubergenone</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1978-10-01</date><risdate>1978</risdate><volume>56</volume><issue>19</issue><spage>2508</spage><epage>2512</epage><pages>2508-2512</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>Syntheses of 4-epi-aubergenone, a sesquiterpenoid related to eudesmane, are described. One synthesis afforded this sesquiterpenoid as a racemate (
12
) whereas another, utilizing (+)-carissone as starting material, afforded an enantiomer (
12
a). The fact that naturally occurring aubergenone is the C(4) epimer of the thermodynamically more stable synthetic
12
was revealed by the discovery that it was completely converted into the latter by treatment with base. This epimeric relationship is substantiated by comparison of the nmr spectra of the two isomers. Evidence requiring the reformulation of the structure of aubergenone as
13
is adduced.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v78-411</doi><tpages>5</tpages></addata></record> |
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| source | NRC Research Press; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| title | A revised structure for aubergenone, a sesquiterpenoid related to eudesmane: synthesis of 4-epi-aubergenone |
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