Selective ring-opening carbonylation of epoxy-steroids
Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co 2(CO) 8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each ca...
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| Veröffentlicht in: | Steroids 2004-04, Vol.69 (4), p.271-277 |
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| container_end_page | 277 |
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| container_issue | 4 |
| container_start_page | 271 |
| container_title | Steroids |
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| creator | Balázs, Attila Benedek, Csilla Szalontai, Gábor Tőrös, Szilárd |
| description | Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co
2(CO)
8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides. |
| doi_str_mv | 10.1016/j.steroids.2004.02.003 |
| format | Article |
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8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2004.02.003</identifier><identifier>PMID: 15183693</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Alkoxycarbonylation ; Asymmetric ring-opening ; Biological and medical sciences ; Catalysis ; Chromatography, Gas ; Chromatography, Thin Layer ; Cobalt ; Epoxy Compounds - chemistry ; Epoxy-steroid ; Fundamental and applied biological sciences. Psychology ; Furans - chemistry ; Homogeneous catalysis ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Solutions ; Stereoisomerism ; Steroids - chemistry ; Structure-Activity Relationship ; Substrate Specificity ; Vertebrates: endocrinology</subject><ispartof>Steroids, 2004-04, Vol.69 (4), p.271-277</ispartof><rights>2004 Elsevier Inc.</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c394t-edcfab5d5eeec3d9cc2e7776ee2d4399f5400d1449ead6f00eaa4fd1faab36463</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2004.02.003$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15884617$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15183693$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Balázs, Attila</creatorcontrib><creatorcontrib>Benedek, Csilla</creatorcontrib><creatorcontrib>Szalontai, Gábor</creatorcontrib><creatorcontrib>Tőrös, Szilárd</creatorcontrib><title>Selective ring-opening carbonylation of epoxy-steroids</title><title>Steroids</title><addtitle>Steroids</addtitle><description>Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co
2(CO)
8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides.</description><subject>Alkoxycarbonylation</subject><subject>Asymmetric ring-opening</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Chromatography, Gas</subject><subject>Chromatography, Thin Layer</subject><subject>Cobalt</subject><subject>Epoxy Compounds - chemistry</subject><subject>Epoxy-steroid</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Furans - chemistry</subject><subject>Homogeneous catalysis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Solutions</subject><subject>Stereoisomerism</subject><subject>Steroids - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtKAzEUhoMotl5eoXSjuxlPJpnMZKeINxBcqOAupMmJpEwnNZmKfXsjbdGdqwOH7z-Xj5AJhZICFRfzMg0Yg7eprAB4CVUJwPbImLZNW9StaPbJOHdkQav2bUSOUpoDgGCyOiQjWtOWCcnGRDxjh2bwnziNvn8vwhL7XKdGx1no150efOinwU1xGb7WxW7pCTlwukt4uq3H5PX25uX6vnh8unu4vnosDJN8KNAap2e1rRHRMCuNqbBpGoFYWc6kdDUHsJRzidoKB4Bac2ep03rGBBfsmJxv5i5j-FhhGtTCJ4Ndp3sMq6Sa_LxkFWRQbEATQ0oRnVpGv9BxrSioH2NqrnbHqx9jCiqV_eTgZLthNVug_Y1tFWXgbAvoZHTnou6NT3-4tuWCNpm73HCYfXx6jCoZj71B62M2rGzw_93yDYJUjxI</recordid><startdate>20040401</startdate><enddate>20040401</enddate><creator>Balázs, Attila</creator><creator>Benedek, Csilla</creator><creator>Szalontai, Gábor</creator><creator>Tőrös, Szilárd</creator><general>Elsevier Inc</general><general>Elsevier Science</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>20040401</creationdate><title>Selective ring-opening carbonylation of epoxy-steroids</title><author>Balázs, Attila ; Benedek, Csilla ; Szalontai, Gábor ; Tőrös, Szilárd</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c394t-edcfab5d5eeec3d9cc2e7776ee2d4399f5400d1449ead6f00eaa4fd1faab36463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Alkoxycarbonylation</topic><topic>Asymmetric ring-opening</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Chromatography, Gas</topic><topic>Chromatography, Thin Layer</topic><topic>Cobalt</topic><topic>Epoxy Compounds - chemistry</topic><topic>Epoxy-steroid</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Furans - chemistry</topic><topic>Homogeneous catalysis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Solutions</topic><topic>Stereoisomerism</topic><topic>Steroids - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Balázs, Attila</creatorcontrib><creatorcontrib>Benedek, Csilla</creatorcontrib><creatorcontrib>Szalontai, Gábor</creatorcontrib><creatorcontrib>Tőrös, Szilárd</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>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Balázs, Attila</au><au>Benedek, Csilla</au><au>Szalontai, Gábor</au><au>Tőrös, Szilárd</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective ring-opening carbonylation of epoxy-steroids</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2004-04-01</date><risdate>2004</risdate><volume>69</volume><issue>4</issue><spage>271</spage><epage>277</epage><pages>271-277</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co
2(CO)
8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>15183693</pmid><doi>10.1016/j.steroids.2004.02.003</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-128X |
| ispartof | Steroids, 2004-04, Vol.69 (4), p.271-277 |
| issn | 0039-128X 1878-5867 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Alkoxycarbonylation Asymmetric ring-opening Biological and medical sciences Catalysis Chromatography, Gas Chromatography, Thin Layer Cobalt Epoxy Compounds - chemistry Epoxy-steroid Fundamental and applied biological sciences. Psychology Furans - chemistry Homogeneous catalysis Magnetic Resonance Spectroscopy Molecular Structure Solutions Stereoisomerism Steroids - chemistry Structure-Activity Relationship Substrate Specificity Vertebrates: endocrinology |
| title | Selective ring-opening carbonylation of epoxy-steroids |
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