The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives
Intramolecular [2 + 2] photoannulation catalysed by copper(i)triflate has been applied to a series of carbohydrate derivatives obtained from glucose. Dienes 1a and 1b lead to cyclobutanes 3a and 3b whereas the diastereoisomeric dienes 5a and 5b gave diastereoisomeric products 7a and 7b. These result...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2004-04, Vol.2 (7), p.1093-1097 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Holt, David J Barker, William D Ghosh, Subrata Jenkins, Paul R |
| description | Intramolecular [2 + 2] photoannulation catalysed by copper(i)triflate has been applied to a series of carbohydrate derivatives obtained from glucose. Dienes 1a and 1b lead to cyclobutanes 3a and 3b whereas the diastereoisomeric dienes 5a and 5b gave diastereoisomeric products 7a and 7b. These results demonstrate that the reaction is stereospecific. Products 3a and 7a were converted into bromoesters 4 and 9 respectively. The Vasella elimination of 8 lead to the expected bicyclic aldehyde 10 and the ring expanded hydroxy ketone 12. The stereospecific formation of enantiomerically pure spiro annulated carbohydrates 18a and 18b was demonstrated whereas in example 19 no selectivity in the formation of 20 and 21 was observed. |
| doi_str_mv | 10.1039/b315623k |
| format | Article |
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Dienes 1a and 1b lead to cyclobutanes 3a and 3b whereas the diastereoisomeric dienes 5a and 5b gave diastereoisomeric products 7a and 7b. These results demonstrate that the reaction is stereospecific. Products 3a and 7a were converted into bromoesters 4 and 9 respectively. The Vasella elimination of 8 lead to the expected bicyclic aldehyde 10 and the ring expanded hydroxy ketone 12. The stereospecific formation of enantiomerically pure spiro annulated carbohydrates 18a and 18b was demonstrated whereas in example 19 no selectivity in the formation of 20 and 21 was observed.</description><identifier>ISSN: 1477-0520</identifier><identifier>DOI: 10.1039/b315623k</identifier><identifier>PMID: 15034635</identifier><language>eng</language><publisher>England</publisher><subject>Carbohydrate Conformation ; Carbohydrates - chemical synthesis ; Catalysis ; Copper - chemistry ; Glucose - analogs & derivatives ; Glucose - chemistry ; Molecular Sequence Data ; Oxidation-Reduction ; Photochemistry ; Stereoisomerism</subject><ispartof>Organic & biomolecular chemistry, 2004-04, Vol.2 (7), p.1093-1097</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15034635$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Holt, David J</creatorcontrib><creatorcontrib>Barker, William D</creatorcontrib><creatorcontrib>Ghosh, Subrata</creatorcontrib><creatorcontrib>Jenkins, Paul R</creatorcontrib><title>The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Intramolecular [2 + 2] photoannulation catalysed by copper(i)triflate has been applied to a series of carbohydrate derivatives obtained from glucose. Dienes 1a and 1b lead to cyclobutanes 3a and 3b whereas the diastereoisomeric dienes 5a and 5b gave diastereoisomeric products 7a and 7b. These results demonstrate that the reaction is stereospecific. Products 3a and 7a were converted into bromoesters 4 and 9 respectively. The Vasella elimination of 8 lead to the expected bicyclic aldehyde 10 and the ring expanded hydroxy ketone 12. The stereospecific formation of enantiomerically pure spiro annulated carbohydrates 18a and 18b was demonstrated whereas in example 19 no selectivity in the formation of 20 and 21 was observed.</description><subject>Carbohydrate Conformation</subject><subject>Carbohydrates - chemical synthesis</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Glucose - analogs & derivatives</subject><subject>Glucose - chemistry</subject><subject>Molecular Sequence Data</subject><subject>Oxidation-Reduction</subject><subject>Photochemistry</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1kMtOwzAQRb0A0VKQ-ALkFYJFwY5fyRIhHpUqsSnryLGnTSCJgx-V8ht8Makoq5m5c3RGGoSuKLmnhBUPFaNCZuzrBM0pV2pJREZm6DyET0JooSQ_QzMqCOOSiTn62dSAw9jHGkITsNvibQpgse4tDkPj3dT1qdVxyoz2latH66cJh-iTiclDwCk0_Q4bNwzgb1d3Exd1Ox4sTR-97lwLZlJ4PNQuuqOvcf3h2q5NxgXAFnyzn9I9hAt0utVtgMtjXaCPl-fN09ty_f66enpcL4eMqLjMRUaF0hUxUnBqqSkqzqw0lBVAeWGY5DnPgU1rYY0qeKYF47lUFnhBWM4W6ObPO3j3nSDEsmuCgbbVPbgUSkWVZEXOJvD6CKaqA1sOvum0H8v_L7JfBAh0TQ</recordid><startdate>20040407</startdate><enddate>20040407</enddate><creator>Holt, David J</creator><creator>Barker, William D</creator><creator>Ghosh, Subrata</creator><creator>Jenkins, Paul R</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20040407</creationdate><title>The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives</title><author>Holt, David J ; Barker, William D ; Ghosh, Subrata ; Jenkins, Paul R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p207t-852157ab0c6541d1c9b43d6c139e149c364848e3c655dc7942a534867de490383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Carbohydrate Conformation</topic><topic>Carbohydrates - chemical synthesis</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Glucose - analogs & derivatives</topic><topic>Glucose - chemistry</topic><topic>Molecular Sequence Data</topic><topic>Oxidation-Reduction</topic><topic>Photochemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Holt, David J</creatorcontrib><creatorcontrib>Barker, William D</creatorcontrib><creatorcontrib>Ghosh, Subrata</creatorcontrib><creatorcontrib>Jenkins, Paul R</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Holt, David J</au><au>Barker, William D</au><au>Ghosh, Subrata</au><au>Jenkins, Paul R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2004-04-07</date><risdate>2004</risdate><volume>2</volume><issue>7</issue><spage>1093</spage><epage>1097</epage><pages>1093-1097</pages><issn>1477-0520</issn><abstract>Intramolecular [2 + 2] photoannulation catalysed by copper(i)triflate has been applied to a series of carbohydrate derivatives obtained from glucose. 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| ispartof | Organic & biomolecular chemistry, 2004-04, Vol.2 (7), p.1093-1097 |
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| source | MEDLINE; Royal Society of Chemistry Journals Archive; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Carbohydrate Conformation Carbohydrates - chemical synthesis Catalysis Copper - chemistry Glucose - analogs & derivatives Glucose - chemistry Molecular Sequence Data Oxidation-Reduction Photochemistry Stereoisomerism |
| title | The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives |
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