Source:http://linkedlifedata.com/resource/pubmed/id/18729372
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
18
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pubmed:dateCreated |
2008-9-11
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pubmed:abstractText |
A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto-, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/3-hydroxybutanal,
http://linkedlifedata.com/resource/pubmed/chemical/Aldehydes,
http://linkedlifedata.com/resource/pubmed/chemical/Carbohydrates,
http://linkedlifedata.com/resource/pubmed/chemical/Enzyme Inhibitors,
http://linkedlifedata.com/resource/pubmed/chemical/Inositol,
http://linkedlifedata.com/resource/pubmed/chemical/Ketones,
http://linkedlifedata.com/resource/pubmed/chemical/alpha-Glucosidases,
http://linkedlifedata.com/resource/pubmed/chemical/validoxylamine G,
http://linkedlifedata.com/resource/pubmed/chemical/valiolamine,
http://linkedlifedata.com/resource/pubmed/chemical/voglibose
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
1523-7052
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
18
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pubmed:volume |
10
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
4137-9
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pubmed:meshHeading | |
pubmed:year |
2008
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pubmed:articleTitle |
Intramolecular direct aldol reactions of sugar diketones: syntheses of valiolamine and validoxylamine G.
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pubmed:affiliation |
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, China. tonyshing@cuhk.edu.hk
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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