Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine
We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57−76% yields and with 4−8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cyclohepteno...
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| Veröffentlicht in: | Journal of organic chemistry 2003-04, Vol.68 (8), p.3049-3054 |
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| container_title | Journal of organic chemistry |
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| creator | Posner, Gary H Maxwell, John P Kahraman, Mehmet |
| description | We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57−76% yields and with 4−8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60−62% yields and with 32−95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the γ-hydroxyketone (GHK) aglycon of the natural product curculigine. |
| doi_str_mv | 10.1021/jo020744q |
| format | Article |
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Chem</addtitle><description>We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57−76% yields and with 4−8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60−62% yields and with 32−95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the γ-hydroxyketone (GHK) aglycon of the natural product curculigine.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry, Organic - methods</subject><subject>Epoxy Compounds - chemistry</subject><subject>Exact sciences and technology</subject><subject>Indicators and Reagents</subject><subject>Ketones - chemistry</subject><subject>Kinetics</subject><subject>Lignans - analysis</subject><subject>Lignans - chemical synthesis</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1v1DAQhi0EokvhwB9AvlAJqSn-SGL3uFq1fC0UlL1btjMpLlk7tR3UPfHXMdpV98JcPNY8ejXzIPSakgtKGH1_Fwgjoq7vn6AFbRip2ktSP0ULQhirOGv5CXqR0h0p1TTNc3RCWSulEHSB_nx1Y3-Or3XK51j7HncZIoQEI9jsfgO-msKD6wHfTOCdv8Vmh79ADr5MfBh1Brz0Lvh0gZfTNDqrc_nhHHC38_knJJdwGHDp8LcQR3frtcerOdq59M7DS_Rs0GOCV4f3FHXXV5vVx2p98-HTarmuNBeXudLCGMkN55bWPWcGxCCo4XKgANDoAvG2KedCa3QRIG250PKWgClV81N0tk-dYrifIWW1dcnCOGoPYU5KcCplw3gB3-1BG0NKEQY1RbfVcacoUf9cq0fXhX1zCJ3NFvojeZBbgLcHQCerxyFqb106crWoGZescNWecynDw-Ncx1-qFVw0avO9U2u22sjuh1Cfj7naprLPHH0x958F_wLXEaLh</recordid><startdate>20030418</startdate><enddate>20030418</enddate><creator>Posner, Gary H</creator><creator>Maxwell, John P</creator><creator>Kahraman, Mehmet</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20030418</creationdate><title>Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine</title><author>Posner, Gary H ; Maxwell, John P ; Kahraman, Mehmet</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-a7bb83b33c14d32be7f71b38f1eee5aa37365002e6ba5208c126c360ebbbb43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry, Organic - methods</topic><topic>Epoxy Compounds - chemistry</topic><topic>Exact sciences and technology</topic><topic>Indicators and Reagents</topic><topic>Ketones - chemistry</topic><topic>Kinetics</topic><topic>Lignans - analysis</topic><topic>Lignans - chemical synthesis</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Posner, Gary H</creatorcontrib><creatorcontrib>Maxwell, John P</creatorcontrib><creatorcontrib>Kahraman, Mehmet</creatorcontrib><collection>Istex</collection><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>Posner, Gary H</au><au>Maxwell, John P</au><au>Kahraman, Mehmet</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-04-18</date><risdate>2003</risdate><volume>68</volume><issue>8</issue><spage>3049</spage><epage>3054</epage><pages>3049-3054</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57−76% yields and with 4−8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60−62% yields and with 32−95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the γ-hydroxyketone (GHK) aglycon of the natural product curculigine.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12688771</pmid><doi>10.1021/jo020744q</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2003-04, Vol.68 (8), p.3049-3054 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Catalysis Chemistry Chemistry, Organic - methods Epoxy Compounds - chemistry Exact sciences and technology Indicators and Reagents Ketones - chemistry Kinetics Lignans - analysis Lignans - chemical synthesis Molecular Structure Nuclear Magnetic Resonance, Biomolecular Organic chemistry Preparations and properties Stereoisomerism |
| title | Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine |
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