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Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*

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Title Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*
 
Creator Sinha, Arun K
Joshi, B P
Sharma, A
Kumar, V
Acharya, Ruchi
 
Subject Natural Product Chemistry
 
Description A microwave-assisted mild protocol is developed for the synthesis of 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an analogue of whisky lactone, from dihydrotagetone, an acyclic monoterpenoid obtained from Tagetes minuta. The methodology involved oxidation of dihydrotagetone in the presence of sodium metaperiodate/potassium permanganate/alumina to give 2,6-dimethyl-4-oxo-heptanoic acid, which upon reduction and subsequent lactonization provided 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone. The reaction is also conducted under conventional conditions and is compared with the microwave method.
 
Date 2007
 
Type Article
PeerReviewed
 
Identifier Sinha, Arun K and Joshi, B P and Sharma, A and Kumar, V and Acharya, Ruchi (2007) Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*. Australian Journal of Chemistry, 60 (2). pp. 124-127.
 
Relation http://ihbt.csircentral.net/657/