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Naphthalene Analogues of Lignans
The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these...
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| Published in: | Journal of organic chemistry 2003-02, Vol.68 (3), p.854-864 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-a379t-c2c0dec6b303aecae9de357724f5cc675d44ef7d782f15a26f66cb4ba52b66633 |
| container_end_page | 864 |
| container_issue | 3 |
| container_start_page | 854 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Madrigal, Blanca Puebla, Pilar Peláez, Rafael Caballero, Esther Medarde, Manuel |
| description | The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring. |
| doi_str_mv | 10.1021/jo0263364 |
| format | article |
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Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. 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Org. Chem</addtitle><description>The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring.</description><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry, Organic - methods</subject><subject>Cyclization</subject><subject>Esterification</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Indicators and Reagents</subject><subject>Lignans - chemical synthesis</subject><subject>Lignans - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - chemistry</subject><subject>Organic chemistry</subject><subject>Podophyllotoxin - chemical synthesis</subject><subject>Podophyllotoxin - chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNptkE1PwkAQhjdGI4ge_AOGiyYeqtv9pEdCFDWNHwHPm-l2F4qlxd020X_vEhq4OJc5zJM3z7wIXcb4LsYkvl_VmAhKBTtC_ZgTHIkEs2PUx5iQiIZTD515v8JhOOenqBcTzkcMyz4avsJm2SyhNJUZjiso60Vr_LC2w7RYVFD5c3RiofTmotsD9Pn4MJ88Renb9HkyTiOgMmkiTTTOjRYZxRSMBpPkhnIpCbNcayF5zpixMpcjYmMORFghdMYy4CQTIsgP0M0ud-Pq76DQqHXhtSlLqEzdeiVJkmApcQBvd6B2tffOWLVxxRrcr4qx2tah9nUE9qoLbbO1yQ9k938ArjsAvIbSOqh04Q8c40RwsrWLdlzhG_Ozv4P7UkJSydX8fabS6eSF4dlUfRxyQfvg07rQrP9H8A8LE4BR</recordid><startdate>20030207</startdate><enddate>20030207</enddate><creator>Madrigal, Blanca</creator><creator>Puebla, Pilar</creator><creator>Peláez, Rafael</creator><creator>Caballero, Esther</creator><creator>Medarde, Manuel</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>20030207</creationdate><title>Naphthalene Analogues of Lignans</title><author>Madrigal, Blanca ; Puebla, Pilar ; Peláez, Rafael ; Caballero, Esther ; Medarde, Manuel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-c2c0dec6b303aecae9de357724f5cc675d44ef7d782f15a26f66cb4ba52b66633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry, Organic - methods</topic><topic>Cyclization</topic><topic>Esterification</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Indicators and Reagents</topic><topic>Lignans - chemical synthesis</topic><topic>Lignans - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - chemistry</topic><topic>Organic chemistry</topic><topic>Podophyllotoxin - chemical synthesis</topic><topic>Podophyllotoxin - chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Madrigal, Blanca</creatorcontrib><creatorcontrib>Puebla, Pilar</creatorcontrib><creatorcontrib>Peláez, Rafael</creatorcontrib><creatorcontrib>Caballero, Esther</creatorcontrib><creatorcontrib>Medarde, Manuel</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>Madrigal, Blanca</au><au>Puebla, Pilar</au><au>Peláez, Rafael</au><au>Caballero, Esther</au><au>Medarde, Manuel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Naphthalene Analogues of Lignans</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-02-07</date><risdate>2003</risdate><volume>68</volume><issue>3</issue><spage>854</spage><epage>864</epage><pages>854-864</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><notes>istex:51D5749B2F1FB9249DA6C41A64C14FB155CA990B</notes><notes>ark:/67375/TPS-LGCJ40SG-Q</notes><notes>This paper is dedicated in memory of our colleague Dr. Benedicto del Rey.</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12558407</pmid><doi>10.1021/jo0263364</doi><tpages>11</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2003-02, Vol.68 (3), p.854-864 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Carbazoles - chemical synthesis Carbazoles - chemistry Catalysis Chemistry Chemistry, Organic - methods Cyclization Esterification Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Indicators and Reagents Lignans - chemical synthesis Lignans - chemistry Magnetic Resonance Spectroscopy Molecular Structure Naphthalenes - chemical synthesis Naphthalenes - chemistry Organic chemistry Podophyllotoxin - chemical synthesis Podophyllotoxin - chemistry Preparations and properties Stereoisomerism |
| title | Naphthalene Analogues of Lignans |
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