On the Synthesis of Protopine Alkaloids
For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3]benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last ste...
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| Veröffentlicht in: | Journal of organic chemistry 2007-09, Vol.72 (19), p.7301-7306 |
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| container_issue | 19 |
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| container_title | Journal of organic chemistry |
| container_volume | 72 |
| creator | Wada, Yasuhiro Kaga, Harumi Uchiito, Shiho Kumazawa, Eri Tomiki, Miho Onozaki, Yu Kurono, Nobuhito Tokuda, Masao Ohkuma, Takeshi Orito, Kazuhiko |
| description | For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3]benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last step for completion of the synthesis. The key substances, indeno[2,1-a][3]benzazepines, were prepared by Bischler−Napieralski cyclization of alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined. |
| doi_str_mv | 10.1021/jo071038y |
| format | Article |
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The key substances, indeno[2,1-a][3]benzazepines, were prepared by Bischler−Napieralski cyclization of alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo071038y</identifier><identifier>PMID: 17705430</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Benzazepines - chemistry ; Benzophenanthridines - chemical synthesis ; Berberine Alkaloids - chemical synthesis ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2007-09, Vol.72 (19), p.7301-7306</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-c99cbda9588b00f403e26c92475eb8fb73464a7a0c2f7dbda72c6c1762d58fd83</citedby><cites>FETCH-LOGICAL-a381t-c99cbda9588b00f403e26c92475eb8fb73464a7a0c2f7dbda72c6c1762d58fd83</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/jo071038y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo071038y$$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=19081485$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17705430$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wada, Yasuhiro</creatorcontrib><creatorcontrib>Kaga, Harumi</creatorcontrib><creatorcontrib>Uchiito, Shiho</creatorcontrib><creatorcontrib>Kumazawa, Eri</creatorcontrib><creatorcontrib>Tomiki, Miho</creatorcontrib><creatorcontrib>Onozaki, Yu</creatorcontrib><creatorcontrib>Kurono, Nobuhito</creatorcontrib><creatorcontrib>Tokuda, Masao</creatorcontrib><creatorcontrib>Ohkuma, Takeshi</creatorcontrib><creatorcontrib>Orito, Kazuhiko</creatorcontrib><title>On the Synthesis of Protopine Alkaloids</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3]benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last step for completion of the synthesis. The key substances, indeno[2,1-a][3]benzazepines, were prepared by Bischler−Napieralski cyclization of alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined.</description><subject>Benzazepines - chemistry</subject><subject>Benzophenanthridines - chemical synthesis</subject><subject>Berberine Alkaloids - chemical synthesis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9PwjAUB_DGaATRg_-A2UWNh-lru_7YkaCogQgJmHhruq6Lg7FhOxL5762ByMV3eYf3yTcvX4QuMdxjIPhh0YDAQOX2CHUxIxDzFJJj1AUgJKaE0w46834BYRhjp6iDhQCWUOii20kdtZ82mm3rsHzpo6aIpq5pm3VZ26hfLXXVlLk_RyeFrry92O8eeh8-zQcv8Xjy_Droj2NNJW5jk6Ymy3XKpMwAigSoJdykJBHMZrLIBE14ooUGQwqRBymI4QYLTnImi1zSHrrZ5a5d87WxvlWr0htbVbq2zcYrLklCBfAA73bQuMZ7Zwu1duVKu63CoH5bUX-tBHu1D91kK5sf5L6GAK73QHujq8Lp2pT-4FKQOJEsuHjnSt_a77-7dkvFBRVMzaczRUf07WP6OFSjQ642PvyzcXXo7p8HfwBXlINa</recordid><startdate>20070914</startdate><enddate>20070914</enddate><creator>Wada, Yasuhiro</creator><creator>Kaga, Harumi</creator><creator>Uchiito, Shiho</creator><creator>Kumazawa, Eri</creator><creator>Tomiki, Miho</creator><creator>Onozaki, Yu</creator><creator>Kurono, Nobuhito</creator><creator>Tokuda, Masao</creator><creator>Ohkuma, Takeshi</creator><creator>Orito, Kazuhiko</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>20070914</creationdate><title>On the Synthesis of Protopine Alkaloids</title><author>Wada, Yasuhiro ; Kaga, Harumi ; Uchiito, Shiho ; Kumazawa, Eri ; Tomiki, Miho ; Onozaki, Yu ; Kurono, Nobuhito ; Tokuda, Masao ; Ohkuma, Takeshi ; Orito, Kazuhiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-c99cbda9588b00f403e26c92475eb8fb73464a7a0c2f7dbda72c6c1762d58fd83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Benzazepines - chemistry</topic><topic>Benzophenanthridines - chemical synthesis</topic><topic>Berberine Alkaloids - chemical synthesis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wada, Yasuhiro</creatorcontrib><creatorcontrib>Kaga, Harumi</creatorcontrib><creatorcontrib>Uchiito, Shiho</creatorcontrib><creatorcontrib>Kumazawa, Eri</creatorcontrib><creatorcontrib>Tomiki, Miho</creatorcontrib><creatorcontrib>Onozaki, Yu</creatorcontrib><creatorcontrib>Kurono, Nobuhito</creatorcontrib><creatorcontrib>Tokuda, Masao</creatorcontrib><creatorcontrib>Ohkuma, Takeshi</creatorcontrib><creatorcontrib>Orito, Kazuhiko</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>Wada, Yasuhiro</au><au>Kaga, Harumi</au><au>Uchiito, Shiho</au><au>Kumazawa, Eri</au><au>Tomiki, Miho</au><au>Onozaki, Yu</au><au>Kurono, Nobuhito</au><au>Tokuda, Masao</au><au>Ohkuma, Takeshi</au><au>Orito, Kazuhiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On the Synthesis of Protopine Alkaloids</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| ispartof | Journal of organic chemistry, 2007-09, Vol.72 (19), p.7301-7306 |
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| source | ACS Publications; MEDLINE |
| subjects | Benzazepines - chemistry Benzophenanthridines - chemical synthesis Berberine Alkaloids - chemical synthesis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | On the Synthesis of Protopine Alkaloids |
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