Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine
The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspid...
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| Veröffentlicht in: | Organic letters 2012-11, Vol.14 (22), p.5621-5623 |
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| container_title | Organic letters |
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| creator | Tan, Shen H Banwell, Martin G Willis, Anthony C Reekie, Tristan A |
| description | The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13]. |
| doi_str_mv | 10.1021/ol3026846 |
| format | Article |
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Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].</description><subject>Aspidosperma - chemistry</subject><subject>Carbazoles</subject><subject>Chemistry, Organic - methods</subject><subject>Cobalt - chemistry</subject><subject>Cyclization</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemistry</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Plant Bark - chemistry</subject><subject>Stereoisomerism</subject><subject>Venezuela</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9u1DAQxi0EoqVw4AWQL0jtIeA_rO09Riv-SYtAZe_RxJ4IFycOsVMpvFVfgSfD3ZQ9cfJo5jff6PNHyEvO3nAm-NsYJBPKvFOPyDnfCFlpthGPT7ViZ-RZSjeM8dLZPiVnQnKm5Eadk7t6HIO3kH0caOwo0GsYcKl2sYWQqy_oPGR09ACDw55eo5tt9rdId4sN_ve6922KOdoYaI70EDME-n0Z8g9MmO41S0XrNHoX04hTD7QOPyFE7xK9_HN3Ve19D8eJd35AWi6tfV7VFvMS4LgLoT3On5MnHYSELx7eC3L48P6w-1Ttv378vKv3FUjDcwW2VdtiWKBG1OA6g2xruNRGWq2Ncpa3nelaoxhIbE3bgQCljNNCCqPlBblcZccp_pox5ab3yWII5XvinBrONTd6U5QKerWidoopTdg141QsTUvDWXMfUHMKqLCvHmTntkd3Iv8lUoDXKwA2NTdxnoZi8j9CfwFnCJrC</recordid><startdate>20121116</startdate><enddate>20121116</enddate><creator>Tan, Shen H</creator><creator>Banwell, Martin G</creator><creator>Willis, Anthony C</creator><creator>Reekie, Tristan A</creator><general>American Chemical Society</general><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>20121116</creationdate><title>Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine</title><author>Tan, Shen H ; Banwell, Martin G ; Willis, Anthony C ; Reekie, Tristan A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-acb690112e7ee7adf8e09813783c7786dc1bf8fb860a3eb8bfa2a668d7232873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aspidosperma - chemistry</topic><topic>Carbazoles</topic><topic>Chemistry, Organic - methods</topic><topic>Cobalt - chemistry</topic><topic>Cyclization</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemistry</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Plant Bark - chemistry</topic><topic>Stereoisomerism</topic><topic>Venezuela</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Shen H</creatorcontrib><creatorcontrib>Banwell, Martin G</creatorcontrib><creatorcontrib>Willis, Anthony C</creatorcontrib><creatorcontrib>Reekie, Tristan A</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Shen H</au><au>Banwell, Martin G</au><au>Willis, Anthony C</au><au>Reekie, Tristan A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2012-11-16</date><risdate>2012</risdate><volume>14</volume><issue>22</issue><spage>5621</spage><epage>5623</epage><pages>5621-5623</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23106356</pmid><doi>10.1021/ol3026846</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-11, Vol.14 (22), p.5621-5623 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1171875786 |
| source | ACS Publications; MEDLINE |
| subjects | Aspidosperma - chemistry Carbazoles Chemistry, Organic - methods Cobalt - chemistry Cyclization Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Molecular Structure Nitriles - chemistry Plant Bark - chemistry Stereoisomerism Venezuela |
| title | Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine |
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