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Volumn 120, Issue 36, 1998, Pages 9228-9236

Ruthenium-catalyzed alder ene type reactions. A formal synthesis of alternaric acid

Author keywords

[No Author keywords available]

Indexed keywords

4 PENTYNOIC ACID; ACETIC ACID DERIVATIVE; ALCOHOL; ALKENE; ALKYNE DERIVATIVE; ALTERNARIC ACID; ANTIFUNGAL AGENT; NATURAL PRODUCT; PALLADIUM; PYRONE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 0032538014     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981540n     Document Type: Article
Times cited : (92)

References (38)
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    • Prepared in 67% yield by alkylation of methyl (triphenylphosphoranylidene)acetate with propargyl bromide in ethyl acetate at reflux
    • Prepared in 67% yield by alkylation of methyl (triphenylphosphoranylidene)acetate with propargyl bromide in ethyl acetate at reflux.
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    • Determined by reduction of the ester of 15 (LAH) to form the primary alcohol and formation of the O-methylmandelate ester (DCC, DMAP) which showed a 1.2:1 ratio of diastereomers
    • Determined by reduction of the ester of 15 (LAH) to form the primary alcohol and formation of the O-methylmandelate ester (DCC, DMAP) which showed a 1.2:1 ratio of diastereomers.
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    • Converting 19 derived from both (S)-12 and racemic 12 to 24 allows ready analysis of the diastereomeric purity which, since the asymmetric dihydroxylation proceeds with 98% ee and translates into the enantiopurity of 19.
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