Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline
The synthesis of the Lycopodium alkaloids, (−)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between (R)- or (S)-phenylglycinol and the substitut...
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| Veröffentlicht in: | Journal of organic chemistry 2018-08, Vol.83 (15), p.8364-8375 |
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| container_title | Journal of organic chemistry |
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| creator | Pinto, Alexandre Piccichè, Miriam Griera, Rosa Molins, Elies Bosch, Joan Amat, Mercedes |
| description | The synthesis of the Lycopodium alkaloids, (−)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between (R)- or (S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from (R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the (S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline. |
| doi_str_mv | 10.1021/acs.joc.8b00983 |
| format | Article |
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Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the (S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline.</description><subject>Alcaloides</subject><subject>Alkaloids</subject><subject>Asymmetric synthesis</subject><subject>Catàlisi asimètrica</subject><subject>Enantioselective catalysis</subject><subject>Lactames</subject><subject>Lactams</subject><subject>Síntesi asimètrica</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>XX2</sourceid><recordid>eNp1kc1uEzEUhS1ERUNgzQ55maqd1D_jmTG7EqUUKRJIKWvL47lDXWbGqT1GSp-g6255O56kDgkgIWHJuvLxud_iHITeUDKnhNFzbcL81pl5VRMiK_4MTahgJCskyZ-jCSGMZZwV_Bi9DOGWpCOEeIGOmZR5yZiYoB_rMTYWAnYDHm8Ar7dDGsEmocWfbzr42mtvB8iutxvAq61xG9fY2OOL7pvunG3CO7wc9DBaF6ADM9rv_0BmPx8eT7IF-N7eJxB-f4ZnpyfZGrzXI9y7ficuz7Aeml8fq2hsE7ukvkJHre4CvD7MKfpyubxeXGWrTx8-Li5Wmc4rNmZUVtAIUwtZGk24NE1BBNNUQimBVMKUpmAt1DQ3gpO8kYy2YLgGXtSU8JxPEd1zTYhGeTDgjR6V0_bvY3cZKZnieUVTolM02-9svLuLEEbV22Cg6_QALobkLUhVElHtrOcHvHcheGjVxtuU6lZRonYtqtSiSi2qQ4tp4-0BHusemj_-37Ulw-nesN-Mfkj5_Bf3BKBLqOI</recordid><startdate>20180803</startdate><enddate>20180803</enddate><creator>Pinto, Alexandre</creator><creator>Piccichè, Miriam</creator><creator>Griera, Rosa</creator><creator>Molins, Elies</creator><creator>Bosch, Joan</creator><creator>Amat, Mercedes</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>XX2</scope><orcidid>https://orcid.org/0000-0003-1012-0551</orcidid><orcidid>https://orcid.org/0000-0001-5974-1733</orcidid><orcidid>https://orcid.org/0000-0002-9551-4690</orcidid></search><sort><creationdate>20180803</creationdate><title>Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline</title><author>Pinto, Alexandre ; Piccichè, Miriam ; Griera, Rosa ; Molins, Elies ; Bosch, Joan ; Amat, Mercedes</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a482t-198ed5cb597ca039cd6052a19e79e085c7c62feb14c5304d921fec3ae36b10343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcaloides</topic><topic>Alkaloids</topic><topic>Asymmetric synthesis</topic><topic>Catàlisi asimètrica</topic><topic>Enantioselective catalysis</topic><topic>Lactames</topic><topic>Lactams</topic><topic>Síntesi asimètrica</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pinto, Alexandre</creatorcontrib><creatorcontrib>Piccichè, Miriam</creatorcontrib><creatorcontrib>Griera, Rosa</creatorcontrib><creatorcontrib>Molins, Elies</creatorcontrib><creatorcontrib>Bosch, Joan</creatorcontrib><creatorcontrib>Amat, Mercedes</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Recercat</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pinto, Alexandre</au><au>Piccichè, Miriam</au><au>Griera, Rosa</au><au>Molins, Elies</au><au>Bosch, Joan</au><au>Amat, Mercedes</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2018-08-03</date><risdate>2018</risdate><volume>83</volume><issue>15</issue><spage>8364</spage><epage>8375</epage><pages>8364-8375</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The synthesis of the Lycopodium alkaloids, (−)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between (R)- or (S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from (R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. 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| source | ACS Publications; Recercat |
| subjects | Alcaloides Alkaloids Asymmetric synthesis Catàlisi asimètrica Enantioselective catalysis Lactames Lactams Síntesi asimètrica |
| title | Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline |
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