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rdf:type | |
lifeskim:mentions | |
pubmed:dateCreated |
1988-5-6
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pubmed:abstractText |
The mechanistic and stereochemical features of a new organozinc-based substitution process [heteroatom-C-(R1,R2)-SPh + R3(2)Zn----heteroatom-C-(R1,R2,R3)], first discovered during a total synthesis of the alkaloid mycotoxin alpha-cyclopiazonic acid, are described. Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process. Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
31
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pubmed:volume |
171
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
109-24
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:3442773-Glycosides,
pubmed-meshheading:3442773-Indicators and Reagents,
pubmed-meshheading:3442773-Magnetic Resonance Spectroscopy,
pubmed-meshheading:3442773-Mass Spectrometry,
pubmed-meshheading:3442773-Organometallic Compounds,
pubmed-meshheading:3442773-Spectrophotometry, Infrared,
pubmed-meshheading:3442773-Structure-Activity Relationship,
pubmed-meshheading:3442773-Zinc
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pubmed:year |
1987
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pubmed:articleTitle |
Organometallics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism.
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pubmed:affiliation |
University of Pittsburgh, Department of Chemistry, Pennsylvania 15260.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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