Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis
Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4′′′′)-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4′′′′)-OH by a mixed anhydride method in the presence of 5 or the related orga...
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| Veröffentlicht in: | Journal of organic chemistry 2012-09, Vol.77 (18), p.7850-7857 |
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| container_end_page | 7857 |
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| container_issue | 18 |
| container_start_page | 7850 |
| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Ueda, Yoshihiro Mishiro, Kenji Yoshida, Keisuke Furuta, Takumi Kawabata, Takeo |
| description | Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4′′′′)-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4′′′′)-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3′′′′)-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved. |
| doi_str_mv | 10.1021/jo301007x |
| format | Article |
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Various functionalized acyl groups can be introduced at the C(4′′′′)-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3′′′′)-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo301007x</identifier><identifier>PMID: 22870937</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acylation ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. 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Org. Chem</addtitle><description>Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4′′′′)-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4′′′′)-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3′′′′)-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.</description><subject>Acylation</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Cardiac Glycosides - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Lanatosides - chemical synthesis</subject><subject>Lanatosides - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1LAzEQhoMotlYP_gHJRVDoaj422fQoVatQKIjicZlmk5Ky3dRkK_bfG21tL2YgmcMz75AHoXNKbihh9HbuOaGEFF8HqEsFI5kckPwQdQlhLONM8g46iXFO0hFCHKMOY6ogA1500fuLmTkfTW106z4Nvk9XiM46Da3zDfYWAx5CqBxoPKrX2kdXmT4eQwPtb4-HfTxd40mYQePTFNTr6OIpOrJQR3O2fXvo7fHhdfiUjSej5-HdOIOc0jZTklpeaaoBJBFqYJS1SgnBQeaGVqlUBRSEVsTKgnKpePpBVenUM0YY76GrTe4y-I-ViW25cFGbuobG-FUsKZEDRooNer1BdfAxBmPLZXALCOsElT8ey53HxF5sY1fThal25J-4BFxuAYgaahug0S7uOZkn-SLfc6Bjyl-FJtn4Z-E3zIuFPA</recordid><startdate>20120921</startdate><enddate>20120921</enddate><creator>Ueda, Yoshihiro</creator><creator>Mishiro, Kenji</creator><creator>Yoshida, Keisuke</creator><creator>Furuta, Takumi</creator><creator>Kawabata, Takeo</creator><general>American Chemical Society</general><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>20120921</creationdate><title>Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis</title><author>Ueda, Yoshihiro ; Mishiro, Kenji ; Yoshida, Keisuke ; Furuta, Takumi ; Kawabata, Takeo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-861f3dc1caa60589e8ff88553a64e1d1d18da1a5c80f6713683555ddc71322023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acylation</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Cardiac Glycosides - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Lanatosides - chemical synthesis</topic><topic>Lanatosides - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ueda, Yoshihiro</creatorcontrib><creatorcontrib>Mishiro, Kenji</creatorcontrib><creatorcontrib>Yoshida, Keisuke</creatorcontrib><creatorcontrib>Furuta, Takumi</creatorcontrib><creatorcontrib>Kawabata, Takeo</creatorcontrib><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>Ueda, Yoshihiro</au><au>Mishiro, Kenji</au><au>Yoshida, Keisuke</au><au>Furuta, Takumi</au><au>Kawabata, Takeo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-09-21</date><risdate>2012</risdate><volume>77</volume><issue>18</issue><spage>7850</spage><epage>7857</epage><pages>7850-7857</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4′′′′)-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4′′′′)-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3′′′′)-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22870937</pmid><doi>10.1021/jo301007x</doi><tpages>8</tpages></addata></record> |
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| subjects | Acylation Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Cardiac Glycosides - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Lanatosides - chemical synthesis Lanatosides - chemistry Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis |
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