Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues
Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moder...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2003-07, Vol.1 (13), p.2364-2376 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Anwar, Muhammed Bailey, Jonathan H Dickinson, Laura C Edwards, Hermia J Goswami, Rajesh Moloney, Mark G |
| description | Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues. |
| doi_str_mv | 10.1039/b303924b |
| format | Article |
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In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b303924b</identifier><identifier>PMID: 12945710</identifier><language>eng</language><publisher>England</publisher><subject>Alkylation ; Amino Acids - chemical synthesis ; Chemistry, Organic - methods ; Glycine - analogs & derivatives ; Glycine - chemistry ; Imines - chemistry ; Models, Chemical ; Molecular Structure ; Pyrrolidinones - chemical synthesis ; Pyrrolidonecarboxylic Acid - analogs & derivatives ; Pyrrolidonecarboxylic Acid - chemical synthesis ; Reproducibility of Results ; Stereoisomerism</subject><ispartof>Organic & biomolecular chemistry, 2003-07, Vol.1 (13), p.2364-2376</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c194t-899832c1269e388873150cc25d6450a0ba88895e588542c334b4e35c8f29b2ee3</citedby><cites>FETCH-LOGICAL-c194t-899832c1269e388873150cc25d6450a0ba88895e588542c334b4e35c8f29b2ee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2831,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12945710$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Anwar, Muhammed</creatorcontrib><creatorcontrib>Bailey, Jonathan H</creatorcontrib><creatorcontrib>Dickinson, Laura C</creatorcontrib><creatorcontrib>Edwards, Hermia J</creatorcontrib><creatorcontrib>Goswami, Rajesh</creatorcontrib><creatorcontrib>Moloney, Mark G</creatorcontrib><title>Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.</description><subject>Alkylation</subject><subject>Amino Acids - chemical synthesis</subject><subject>Chemistry, Organic - methods</subject><subject>Glycine - analogs & derivatives</subject><subject>Glycine - chemistry</subject><subject>Imines - chemistry</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Pyrrolidinones - chemical synthesis</subject><subject>Pyrrolidonecarboxylic Acid - analogs & derivatives</subject><subject>Pyrrolidonecarboxylic Acid - chemical synthesis</subject><subject>Reproducibility of Results</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMtKw0AUhgdRbK2CTyBZSV1E55rMuLPFGxQqqOswmZyUkSQTZxIhb29Kgy7OlY__cH6ELgm-JZipu5yNmfL8CM0JT9MYC6aO_3qKZ-gshC-MiUoTfopmhCouUoLnaPs2eO8qW9jGNRCiArz9gSIqvauj5ftN3A7e7aq-07U1kTa2uI9aaGpt_DRHutmHrtyuh3COTkpdBbiY6gJ9Pj1-rF_izfb5df2wiQ1RvIulUpJRQ2iigEkpU0YENoaKIuECa5zrcakECCkFp4YxnnNgwsiSqpwCsAW6Pui23n2Pd7ustsFAVekGXB-ylCVk_FyM4PIAGu9C8FBmrbe19kNGcLY3L1sdzFuN6NWk2ec1FP_g5Bb7BcYXZ-g</recordid><startdate>20030707</startdate><enddate>20030707</enddate><creator>Anwar, Muhammed</creator><creator>Bailey, Jonathan H</creator><creator>Dickinson, Laura C</creator><creator>Edwards, Hermia J</creator><creator>Goswami, Rajesh</creator><creator>Moloney, Mark G</creator><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>20030707</creationdate><title>Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues</title><author>Anwar, Muhammed ; Bailey, Jonathan H ; Dickinson, Laura C ; Edwards, Hermia J ; Goswami, Rajesh ; Moloney, Mark G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c194t-899832c1269e388873150cc25d6450a0ba88895e588542c334b4e35c8f29b2ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alkylation</topic><topic>Amino Acids - chemical synthesis</topic><topic>Chemistry, Organic - methods</topic><topic>Glycine - analogs & derivatives</topic><topic>Glycine - chemistry</topic><topic>Imines - chemistry</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Pyrrolidinones - chemical synthesis</topic><topic>Pyrrolidonecarboxylic Acid - analogs & derivatives</topic><topic>Pyrrolidonecarboxylic Acid - chemical synthesis</topic><topic>Reproducibility of Results</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Anwar, Muhammed</creatorcontrib><creatorcontrib>Bailey, Jonathan H</creatorcontrib><creatorcontrib>Dickinson, Laura C</creatorcontrib><creatorcontrib>Edwards, Hermia J</creatorcontrib><creatorcontrib>Goswami, Rajesh</creatorcontrib><creatorcontrib>Moloney, Mark G</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 & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Anwar, Muhammed</au><au>Bailey, Jonathan H</au><au>Dickinson, Laura C</au><au>Edwards, Hermia J</au><au>Goswami, Rajesh</au><au>Moloney, Mark G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2003-07-07</date><risdate>2003</risdate><volume>1</volume><issue>13</issue><spage>2364</spage><epage>2376</epage><pages>2364-2376</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. 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| ispartof | Organic & biomolecular chemistry, 2003-07, Vol.1 (13), p.2364-2376 |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Royal Society of Chemistry Journals Archive (1841-2007); Alma/SFX Local Collection |
| subjects | Alkylation Amino Acids - chemical synthesis Chemistry, Organic - methods Glycine - analogs & derivatives Glycine - chemistry Imines - chemistry Models, Chemical Molecular Structure Pyrrolidinones - chemical synthesis Pyrrolidonecarboxylic Acid - analogs & derivatives Pyrrolidonecarboxylic Acid - chemical synthesis Reproducibility of Results Stereoisomerism |
| title | Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues |
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