(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.author | Koreeda, Masato | en_US |
dc.contributor.author | Teng, Kelly | en_US |
dc.contributor.author | Murata, Toshiki | en_US |
dc.date.accessioned | 2006-04-10T13:59:48Z | |
dc.date.available | 2006-04-10T13:59:48Z | |
dc.date.issued | 1990 | en_US |
dc.identifier.citation | Koreeda,, 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.uri | http://www.sciencedirect.com/science/article/B6THS-42HFY49-15R/2/af21792678be664c17eb27679a2faf11 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/28968 | |
dc.description.abstract | The 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.extent | 278842 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_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 acid | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.contributor.affiliationum | Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.contributor.affiliationum | Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/28968/1/0000805.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/S0040-4039(00)98012-2 | en_US |
dc.identifier.source | Tetrahedron Letters | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
Files in this item
Remediation of Harmful Language
The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.
Accessibility
If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.