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(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic acid

dc.contributor.authorKoreeda, Masatoen_US
dc.contributor.authorTeng, Kellyen_US
dc.contributor.authorMurata, Toshikien_US
dc.date.accessioned2006-04-10T13:59:48Z
dc.date.available2006-04-10T13:59:48Z
dc.date.issued1990en_US
dc.identifier.citationKoreeda,, Masato, Teng, Kelly, Murata, Toshiki (1990)."(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic acid." Tetrahedron Letters 31(42): 5997-6000. <http://hdl.handle.net/2027.42/28968>en_US
dc.identifier.urihttp://www.sciencedirect.com/science/article/B6THS-42HFY49-15R/2/af21792678be664c17eb27679a2faf11en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/28968
dc.description.abstractThe 5-step synthesis of (+/-)-shikimic acid has been achieved in 55% overall yield from (1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene, starting with its Diels-Alder reaction with 2-(trimethylsilyl)ethyl acrylate and featuring the use of Fleming's one-pot procedure for the conversion of the phenyldimethylsilyl group to the hydroxyl as the salient, pivotal step in the synthesis.en_US
dc.format.extent278842 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherElsevieren_US
dc.title(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic aciden_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A.en_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A.en_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A.en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/28968/1/0000805.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1016/S0040-4039(00)98012-2en_US
dc.identifier.sourceTetrahedron Lettersen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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