Synthesis and Structure Revision of Calyxin Natural Products
Tandem Prins cyclization and Friedel−Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, w...
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| Veröffentlicht in: | Journal of organic chemistry 2006-04, Vol.71 (8), p.3176-3183 |
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| container_end_page | 3183 |
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| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Tian, Xia Jaber, James J Rychnovsky, Scott D |
| description | Tandem Prins cyclization and Friedel−Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations. |
| doi_str_mv | 10.1021/jo060094g |
| format | Article |
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The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo060094g</identifier><identifier>PMID: 16599616</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alpinia - chemistry ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Chemistry ; Cyclization ; Exact sciences and technology ; Molecular Structure ; Morpholines - chemical synthesis ; Morpholines - chemistry ; Organic chemistry ; Oxidation-Reduction ; Seeds - chemistry</subject><ispartof>Journal of organic chemistry, 2006-04, Vol.71 (8), p.3176-3183</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-67ef4ccf0c8c6d127ed7e3e948fc73d2536055847fe19f5d9d0f25fe1d8fa2db3</citedby><cites>FETCH-LOGICAL-a447t-67ef4ccf0c8c6d127ed7e3e948fc73d2536055847fe19f5d9d0f25fe1d8fa2db3</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/jo060094g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo060094g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17747006$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16599616$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tian, Xia</creatorcontrib><creatorcontrib>Jaber, James J</creatorcontrib><creatorcontrib>Rychnovsky, Scott D</creatorcontrib><title>Synthesis and Structure Revision of Calyxin Natural Products</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Tandem Prins cyclization and Friedel−Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.</description><subject>Alpinia - chemistry</subject><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Molecular Structure</subject><subject>Morpholines - chemical synthesis</subject><subject>Morpholines - chemistry</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Seeds - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtKAzEUBuAgitbLwheQ2Si4GE0yuUzAjRRvULTaCuImxFw0Op2pyYy0b29Ki92YzSGcj8PPD8AhgmcIYnT-2UAGoSDvG6CHKIY5E5Bsgh6EGOcFZsUO2I3xE6ZHKd0GO4hRIRhiPXAxmtfth40-Zqo22agNnW67YLMn--Ojb-qscVlfVfOZr7N7lVaqyoahMYnFfbDlVBXtwWrugefrq3H_Nh883Nz1Lwe5IoS3OePWEa0d1KVmBmFuDbeFFaR0mhcG04KlXCXhziLhqBEGOkzTx5ROYfNW7IGT5d1paL47G1s58VHbqlK1bbooGS8LIThL8HQJdWhiDNbJafATFeYSQbmoSv5VlezR6mj3NrFmLVfdJHC8AipqVbmgau3j2nFOOIQLly-dj62d_e1V-ErBCk7leDiSr-PbR_KCXiVZ31U6pjxdqFN3_wT8Be3LjDY</recordid><startdate>20060414</startdate><enddate>20060414</enddate><creator>Tian, Xia</creator><creator>Jaber, James J</creator><creator>Rychnovsky, Scott D</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060414</creationdate><title>Synthesis and Structure Revision of Calyxin Natural Products</title><author>Tian, Xia ; Jaber, James J ; Rychnovsky, Scott D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-67ef4ccf0c8c6d127ed7e3e948fc73d2536055847fe19f5d9d0f25fe1d8fa2db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alpinia - chemistry</topic><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Molecular Structure</topic><topic>Morpholines - chemical synthesis</topic><topic>Morpholines - chemistry</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Seeds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Xia</creatorcontrib><creatorcontrib>Jaber, James J</creatorcontrib><creatorcontrib>Rychnovsky, Scott D</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Tian, Xia</au><au>Jaber, James J</au><au>Rychnovsky, Scott D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Structure Revision of Calyxin Natural Products</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alpinia - chemistry Biological Products - chemical synthesis Biological Products - chemistry Chemistry Cyclization Exact sciences and technology Molecular Structure Morpholines - chemical synthesis Morpholines - chemistry Organic chemistry Oxidation-Reduction Seeds - chemistry |
| title | Synthesis and Structure Revision of Calyxin Natural Products |
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