Source:http://linkedlifedata.com/resource/pubmed/id/12895061
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
16
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| pubmed:dateCreated |
2003-8-4
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| pubmed:abstractText |
The absolute structures of some naturally occurring chiral 2-isopropenyl-2,3-dihydrobenzofurans, (+)-remirol (1a), (+)-remiridiol (1b), (+)-angenomalin (2), and (+)-isoangenomalin (3), were studied by respective chiral synthesis. Kinetic resolutions of racemic 2-isopropenyl-2,3-dihydrobenzofurans, 2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran (4), 4-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran-5-carbaldehyde (8), and 2-isopropenyl-6-(MOM)oxy-2,3-dihydrobenzofuran-5-carbaldehyde (11c), by Sharpless dihydroxylation using (DHQ)(2)AQN or (DHQD)(2)AQN gave the corresponding chiral 2-isopropenyl-2,3-dihydrobenzofurans. Chiral (S)-(+)-4 (99% ee, using (DHQD)(2)AQN) was converted to natural remirol (S)-(+)-1a and then to natural remiridiol (S)-(+)-1b. (S)-(+)-8 (97% ee, using (DHQD)(2)AQN) was converted to natural angenomalin (S)-(+)-2. (R)-(-)-11c (>99% ee, using (DHQ)(2)AQN), was converted to natural isoangenomalin (R)-(+)-3. Thus, the absolute structures of natural remirol (+)-1a and remiridiol (+)-1b and angenomalin (+)-2 were determined to be S, and the structure of natural isoangenomalin (+)-3 was R.
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| 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 |
Aug
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| pubmed:issn |
0022-3263
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
8
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| pubmed:volume |
68
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
6274-8
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| pubmed:dateRevised |
2006-11-15
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| pubmed:meshHeading |
pubmed-meshheading:12895061-Apiaceae,
pubmed-meshheading:12895061-Benzofurans,
pubmed-meshheading:12895061-Chromatography, High Pressure Liquid,
pubmed-meshheading:12895061-Chromatography, Thin Layer,
pubmed-meshheading:12895061-Cyclization,
pubmed-meshheading:12895061-Cyperaceae,
pubmed-meshheading:12895061-Eupatorium,
pubmed-meshheading:12895061-Hydroxylation,
pubmed-meshheading:12895061-Indicators and Reagents,
pubmed-meshheading:12895061-Kinetics,
pubmed-meshheading:12895061-Ligands,
pubmed-meshheading:12895061-Magnetic Resonance Spectroscopy,
pubmed-meshheading:12895061-Mass Spectrometry,
pubmed-meshheading:12895061-Plants,
pubmed-meshheading:12895061-Pyrans,
pubmed-meshheading:12895061-Spectrophotometry, Infrared,
pubmed-meshheading:12895061-Spectroscopy, Fourier Transform Infrared,
pubmed-meshheading:12895061-Stereoisomerism
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| pubmed:year |
2003
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| pubmed:articleTitle |
Absolute structures of some naturally occurring isopropenyldihydrobenzofurans, remirol, remiridiol, angenomalin, and isoangenomalin.
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| pubmed:affiliation |
Department of Chemistry, Faculty of Science, Toyama University, Gofuku, Toyama 930-8555, Japan. seiji@sci.toyama-u.ac.jp
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| pubmed:publicationType |
Journal Article
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