Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL
A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1995/01/15, Vol.43(1), pp.49-52 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | FUJII, Tozo OHBA, Masashi SETO, Shigeki |
| description | A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H2O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid. |
| doi_str_mv | 10.1248/cpb.43.49 |
| format | Article |
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XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H2O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid.</description><subject>Bischler-Napieralski cyclization</subject><subject>Chemistry</subject><subject>cincholoipon</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>lactim ether N-alkylation</subject><subject>Ophiorrhiza alkaloid synthesis</subject><subject>ophiorrhizine configuration</subject><subject>Organic chemistry</subject><subject>oxazolium hydrogenolysis</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><recordid>eNpFUMlu2zAQJYIWiOvmkD8gkB4aoFJJkVp4dN1NgIE0bQL4RoxIqqJLky4pH9x7_rsybCSXmcNb5s1D6JqSnBa8-ah2Xc5ZzsUFmlHG66wsCvYKzQghIitYxS7Rm5Q2hBQlqdkMPd3vrQ_O_rPaepNyvF6v27bN8QIvBxvB4V8HPw4m2YRDj99nt9ndbrAhxmHSePMBA_5h_AjqoJxV-H4Po4ke4gG3Xgdn8ML9AResxn0MW_wiBryFTYj4Z_t59Ra97sElc3Xec_T49cvD8nu2uvvWLherTJWMiUx1QghNmsbUpSJdx-paGMoF46QvgbOeUk5qrrQGIFVdN4XWPeNc667oCFNsjm5OvrsY_u5NGuUm7Ke0LknKK1JUvJlamaPbE0vFkFI0vdxFu51ekpTIY8tyallyJqfLc_Tu7AhJgesjeGXTs4DxKXFFJtqnE22TRvhtnnGIo1XOHA2pKJujKT0P8QIOEKXx7D-MZ5N5</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>FUJII, Tozo</creator><creator>OHBA, Masashi</creator><creator>SETO, Shigeki</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1995</creationdate><title>Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL</title><author>FUJII, Tozo ; OHBA, Masashi ; SETO, Shigeki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5339-cb999d088e75c0bb3779e149340f5a43f114074cddaa067782ddf344ddb2b03c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Bischler-Napieralski cyclization</topic><topic>Chemistry</topic><topic>cincholoipon</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>lactim ether N-alkylation</topic><topic>Ophiorrhiza alkaloid synthesis</topic><topic>ophiorrhizine configuration</topic><topic>Organic chemistry</topic><topic>oxazolium hydrogenolysis</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FUJII, Tozo</creatorcontrib><creatorcontrib>OHBA, Masashi</creatorcontrib><creatorcontrib>SETO, Shigeki</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FUJII, Tozo</au><au>OHBA, Masashi</au><au>SETO, Shigeki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1995</date><risdate>1995</risdate><volume>43</volume><issue>1</issue><spage>49</spage><epage>52</epage><pages>49-52</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H2O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.43.49</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1995/01/15, Vol.43(1), pp.49-52 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_journals_1460264807 |
| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | Bischler-Napieralski cyclization Chemistry cincholoipon Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings lactim ether N-alkylation Ophiorrhiza alkaloid synthesis ophiorrhizine configuration Organic chemistry oxazolium hydrogenolysis Preparations and properties |
| title | Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL |
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