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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
25
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pubmed:dateCreated |
2002-12-6
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pubmed:abstractText |
Chelation-controlled reduction of chiral beta-alkoxy ketones containing a competing beta'-oxygen functionality has been investigated. Various syn-1,3-diols were prepared conveniently by reduction of beta-alkoxy ketones with LiI/LiAlH(4) (syn:anti selectivity up to >99:1). The corresponding beta-alkoxy ketones were derived from nitro-aldol reactions of chiral alkoxy aldehydes with a series of nitro compounds. This methodology is utilized in a short and efficient synthesis of the delta-lactone moiety of the HMG-CoA reductase inhibitors compactin and mevinolin.
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pubmed:grant |
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0022-3263
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
13
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pubmed:volume |
67
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
8783-8
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:12467389-Alcohols,
pubmed-meshheading:12467389-Catalysis,
pubmed-meshheading:12467389-Chelating Agents,
pubmed-meshheading:12467389-Chemistry, Organic,
pubmed-meshheading:12467389-Hydroxymethylglutaryl-CoA Reductase Inhibitors,
pubmed-meshheading:12467389-Indicators and Reagents,
pubmed-meshheading:12467389-Lactones,
pubmed-meshheading:12467389-Lithium,
pubmed-meshheading:12467389-Lovastatin,
pubmed-meshheading:12467389-Molecular Structure,
pubmed-meshheading:12467389-Oxidation-Reduction,
pubmed-meshheading:12467389-Stereoisomerism
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pubmed:year |
2002
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pubmed:articleTitle |
Chelation-controlled reduction: stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone.
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pubmed:affiliation |
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, 60607, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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