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Domino Recombinant gamma-Isomerization and Reverse Wacker Oxidation of gamma-Vinyl-gamma-butyrolactone: Synthesis of (+)-trans-, (-)- and (+)-Disparlures

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Title Domino Recombinant gamma-Isomerization and Reverse Wacker Oxidation of gamma-Vinyl-gamma-butyrolactone: Synthesis of (+)-trans-, (-)- and (+)-Disparlures
 
Creator BETHI, V
KATTANGURU, P
FERNANDES, RA
 
Subject Synthetic methods
Asymmetric synthesis
Cross-metathesis
Palladium
Oxidation
Pheromones
NEIGHBORING OXYGEN FUNCTIONS
GYPSY-MOTH PHEROMONE
OLEFIN CROSS-METATHESIS
ASYMMETRIC DIHYDROXYLATION
ENANTIODIVERGENT SYNTHESIS
DISPARLURE
REGIOCHEMISTRY
ENANTIOMERS
IDENTIFICATION
ALDEHYDES
 
Description A domino palladium-catalyzed recombinant -isomerization and reverse Wacker oxidation of -vinyl--butyrolactone has been explored. The strategy has been used in the stereoselective synthesis of (+)-trans-, (-)- and (+)-disparlures. The synthesis was achieved in seven to eight steps from D-glucono--lactone with overall yields of 19.3, 20.7 and 22.6%, respectively.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T11:19:54Z
2014-12-28T11:19:54Z
2014
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(15)3249-3255
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201400021
http://dspace.library.iitb.ac.in/jspui/handle/100/16342
 
Language English