Synthesis of N-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer
Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2010-04, Vol.2010 (11), p.2206-2211 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2010 |
| creator | Matsushima, Yoshitaka Kino, Jun |
| description | Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described in this paper.
Trichloroacetimidates, which are prepared from osmundalactone and its epimer, unexpectedly undergo silica gel promoted stereoselective intramolecular conjugate addition to produce the oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described. |
| doi_str_mv | 10.1002/ejoc.200901402 |
| format | Article |
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Trichloroacetimidates, which are prepared from osmundalactone and its epimer, unexpectedly undergo silica gel promoted stereoselective intramolecular conjugate addition to produce the oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200901402</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amino sugars ; Analytical chemistry ; Chemistry ; Chromatographic methods and physical methods associated with chromatography ; Exact sciences and technology ; Heterocycles ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Natural products ; Nucleophilic addition ; Organic chemistry ; Preparations and properties</subject><ispartof>European Journal of Organic Chemistry, 2010-04, Vol.2010 (11), p.2206-2211</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3382-77a66f767aff661a82bfcf383df0be92e6ab0103159c81ab3f409d3a8c7721df3</citedby><cites>FETCH-LOGICAL-c3382-77a66f767aff661a82bfcf383df0be92e6ab0103159c81ab3f409d3a8c7721df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.200901402$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200901402$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,776,780,788,1411,27901,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22611942$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsushima, Yoshitaka</creatorcontrib><creatorcontrib>Kino, Jun</creatorcontrib><title>Synthesis of N-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described in this paper.
Trichloroacetimidates, which are prepared from osmundalactone and its epimer, unexpectedly undergo silica gel promoted stereoselective intramolecular conjugate addition to produce the oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described.</description><subject>Amino sugars</subject><subject>Analytical chemistry</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Exact sciences and technology</subject><subject>Heterocycles</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Natural products</subject><subject>Nucleophilic addition</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkU9vEzEQxVcIJErhytkXjg7-s_Wuj22apoGqqWgR3KxZr00dvOvIdgThm_Ht8Col4sZpRqP3ezN-rqq3lMwoIey92QQ9Y4RIQmvCnlUnlEiJiZDkeelrXmMq-deX1auUNqTIhKAn1e_7_ZgfTXIJBYtu8cUvfBdDNjqbHl3iS9iNIcHgRoNgnCafXMp_J90e3TvvNKCl8ahwQ5iw1ZgjDMEbvfMQ0TyMm903yAad973LLozTqofo9KMPMYA22Q2uL4JyQ5ehOPfIFjO0TsNu7MGDzuHpgFVOaLF1g4mvqxcWfDJvnupp9flq8TC_xjfr5Wp-foM15y3DTQNC2EY0YG15MbSss9rylveWdEYyI6AjlHB6JnVLoeO2JrLn0OqmYbS3_LSaHXx1DClFY9U2ugHiXlGipuDVFLw6Bl-AdwdgC0mDtxFG7dKRYkxQKutJJw-6H86b_X9c1eLDev7vDnxgy2-Yn0cW4nclGt6cqS-3S3V3XbOPF4Ipwf8Ab2yn4Q</recordid><startdate>201004</startdate><enddate>201004</enddate><creator>Matsushima, Yoshitaka</creator><creator>Kino, Jun</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201004</creationdate><title>Synthesis of N-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer</title><author>Matsushima, Yoshitaka ; Kino, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3382-77a66f767aff661a82bfcf383df0be92e6ab0103159c81ab3f409d3a8c7721df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Amino sugars</topic><topic>Analytical chemistry</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Exact sciences and technology</topic><topic>Heterocycles</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Natural products</topic><topic>Nucleophilic addition</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsushima, Yoshitaka</creatorcontrib><creatorcontrib>Kino, Jun</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsushima, Yoshitaka</au><au>Kino, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2010-04</date><risdate>2010</risdate><volume>2010</volume><issue>11</issue><spage>2206</spage><epage>2211</epage><pages>2206-2211</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described in this paper.
Trichloroacetimidates, which are prepared from osmundalactone and its epimer, unexpectedly undergo silica gel promoted stereoselective intramolecular conjugate addition to produce the oxazolines in excellent yields. The novel, simple synthesis of N‐Bz‐protected D‐daunosamine and D‐ristosamine from these oxazolines is described.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200901402</doi><tpages>6</tpages></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2010-04, Vol.2010 (11), p.2206-2211 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Amino sugars Analytical chemistry Chemistry Chromatographic methods and physical methods associated with chromatography Exact sciences and technology Heterocycles Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Natural products Nucleophilic addition Organic chemistry Preparations and properties |
| title | Synthesis of N-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer |
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