A Simple, Short, and Flexible Synthesis of Viridiofungin Derivatives
Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geo...
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| Veröffentlicht in: | Journal of organic chemistry 2006-08, Vol.71 (16), p.6185-6191 |
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| container_end_page | 6191 |
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| container_issue | 16 |
| container_start_page | 6185 |
| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Goldup, Stephen M Pilkington, Christopher J White, Andrew J. P Burton, Andrew Barrett, Anthony G. M |
| description | Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C−C bond-forming steps. |
| doi_str_mv | 10.1021/jo060931e |
| format | Article |
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The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C−C bond-forming steps.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo060931e</identifier><identifier>PMID: 16872204</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkylation ; Amino Acids - chemistry ; Catalysis ; Chemistry ; Citrates - chemical synthesis ; Citrates - chemistry ; Esters - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Malates - chemistry ; Molecular Structure ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2006-08, Vol.71 (16), p.6185-6191</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-811588e9b963e4954d50b07ba91c290dc7e733937b432e1406ba953cd1ac82ec3</citedby><cites>FETCH-LOGICAL-a381t-811588e9b963e4954d50b07ba91c290dc7e733937b432e1406ba953cd1ac82ec3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo060931e$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo060931e$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17996950$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16872204$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Goldup, Stephen M</creatorcontrib><creatorcontrib>Pilkington, Christopher J</creatorcontrib><creatorcontrib>White, Andrew J. 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The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C−C bond-forming steps.</description><subject>Alkylation</subject><subject>Amino Acids - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Citrates - chemical synthesis</subject><subject>Citrates - chemistry</subject><subject>Esters - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Malates - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9LwzAUB_Agis7pwX9AelEQVs2PJmmOMt1Uhgqbu4Y0fdVo186kHfrfW9lwF9_lHd6HL48vQicEXxJMydV7jQVWjMAO6hFOcSwUTnZRD2NKY0YFO0CHIbzjbjjn--iAiFRSipMeurmOpm6xLGEQTd9q3wwiU-XRqIQvl5UQTb-r5g2CC1FdRHPnXe7qoq1eXRXdgHcr07gVhCO0V5gywPFm99HL6HY2vIsnT-P74fUkNiwlTZwSwtMUVKYEg0TxJOc4wzIziliqcG4lSMYUk1nCKJAEi-7Emc2JsSkFy_rofJ279PVnC6HRCxcslKWpoG6DFqlIuaS8gxdraH0dgodCL71bGP-tCda_lem_yjp7ugltswXkW7npqANnG2CCNWXhTWVd2DqplFAcdy5eOxca-Pq7G_-hhWSS69nzVI-Hd_MHPp7ox22usaH7p_VV190_D_4A-0uMyQ</recordid><startdate>20060804</startdate><enddate>20060804</enddate><creator>Goldup, Stephen M</creator><creator>Pilkington, Christopher J</creator><creator>White, Andrew J. 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Chem</addtitle><date>2006-08-04</date><risdate>2006</risdate><volume>71</volume><issue>16</issue><spage>6185</spage><epage>6191</epage><pages>6185-6191</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C−C bond-forming steps.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16872204</pmid><doi>10.1021/jo060931e</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2006-08, Vol.71 (16), p.6185-6191 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alkylation Amino Acids - chemistry Catalysis Chemistry Citrates - chemical synthesis Citrates - chemistry Esters - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Malates - chemistry Molecular Structure Organic chemistry Preparations and properties |
| title | A Simple, Short, and Flexible Synthesis of Viridiofungin Derivatives |
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