Novel Rearrangements of Sesquiterpenoid Panasinsane Derivatives under Acidic Conditions
The sesquiterpenoid panasinsane derivatives 11 and 14−16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, −63 °C) have...
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| Veröffentlicht in: | Journal of organic chemistry 2001-06, Vol.66 (12), p.4327-4332 |
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| container_title | Journal of organic chemistry |
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| creator | Amigo, Carlos F. D Collado, Isidro G Hanson, James R Hernández-Galán, Rosario Hitchcock, Peter B Macías-Sánchez, Antonio J Mobbs, Daniel J |
| description | The sesquiterpenoid panasinsane derivatives 11 and 14−16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, −63 °C) have been investigated. The ginsenol derivative 17 is obtained from compounds 11 and 14 under TCNE-catalyzed conditions. The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo[5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed. |
| doi_str_mv | 10.1021/jo0155557 |
| format | Article |
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D ; Collado, Isidro G ; Hanson, James R ; Hernández-Galán, Rosario ; Hitchcock, Peter B ; Macías-Sánchez, Antonio J ; Mobbs, Daniel J</creator><creatorcontrib>Amigo, Carlos F. D ; Collado, Isidro G ; Hanson, James R ; Hernández-Galán, Rosario ; Hitchcock, Peter B ; Macías-Sánchez, Antonio J ; Mobbs, Daniel J</creatorcontrib><description>The sesquiterpenoid panasinsane derivatives 11 and 14−16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, −63 °C) have been investigated. The ginsenol derivative 17 is obtained from compounds 11 and 14 under TCNE-catalyzed conditions. The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo[5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0155557</identifier><identifier>PMID: 11397171</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Hydrogen-Ion Concentration ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry ; Spectrum Analysis</subject><ispartof>Journal of organic chemistry, 2001-06, Vol.66 (12), p.4327-4332</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-3c0c2c6aa20d7b4a3c0aba92abd0540ad5d4811631f4a8619a3b94a08b8cdb0a3</citedby><cites>FETCH-LOGICAL-a349t-3c0c2c6aa20d7b4a3c0aba92abd0540ad5d4811631f4a8619a3b94a08b8cdb0a3</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/jo0155557$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0155557$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11397171$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Amigo, Carlos F. 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The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo[5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed.</description><subject>Hydrogen-Ion Concentration</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><subject>Spectrum Analysis</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EtLAzEQB_AgitbHwS8ge1HwsDrZ7PMorS-QWnzgMcwmU4m2SU12i357Iy16cS7DkB8z4c_YIYczDhk_f3PAi1jVBhvwIoO0bCDfZAOALEtFVoodthvCG8SKapvtcC6aild8wF7Gbkmz5IHQe7SvNCfbhcRNk0cKH73pyC_IOqOTCVoMxga0lIzImyV2Zkkh6a0mn1woo41Khs5q0xlnwz7bmuIs0MG677Hnq8un4U16d399O7y4S1HkTZcKBSpTJWIGumpzjDO22GTYaihyQF3ovOa8FHyaY13yBkXb5Ah1WyvdAoo9drLau_Duo6fQybkJimaz-E_XB1lBw_OqgAhPV1B5F4KnqVx4M0f_JTnInxTlb4rRHq2X9u2c9J9cxxZBugImdPT5-47-XZaVqAr5NHmU4-tmVIiHkayjP155VCHe6b2Nmfxz-BsKXoit</recordid><startdate>20010615</startdate><enddate>20010615</enddate><creator>Amigo, Carlos F. 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D</creatorcontrib><creatorcontrib>Collado, Isidro G</creatorcontrib><creatorcontrib>Hanson, James R</creatorcontrib><creatorcontrib>Hernández-Galán, Rosario</creatorcontrib><creatorcontrib>Hitchcock, Peter B</creatorcontrib><creatorcontrib>Macías-Sánchez, Antonio J</creatorcontrib><creatorcontrib>Mobbs, Daniel J</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amigo, Carlos F. D</au><au>Collado, Isidro G</au><au>Hanson, James R</au><au>Hernández-Galán, Rosario</au><au>Hitchcock, Peter B</au><au>Macías-Sánchez, Antonio J</au><au>Mobbs, Daniel J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Rearrangements of Sesquiterpenoid Panasinsane Derivatives under Acidic Conditions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2001-06-15</date><risdate>2001</risdate><volume>66</volume><issue>12</issue><spage>4327</spage><epage>4332</epage><pages>4327-4332</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The sesquiterpenoid panasinsane derivatives 11 and 14−16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, −63 °C) have been investigated. The ginsenol derivative 17 is obtained from compounds 11 and 14 under TCNE-catalyzed conditions. The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo[5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11397171</pmid><doi>10.1021/jo0155557</doi><tpages>6</tpages></addata></record> |
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| subjects | Hydrogen-Ion Concentration Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Spectrum Analysis |
| title | Novel Rearrangements of Sesquiterpenoid Panasinsane Derivatives under Acidic Conditions |
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