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A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-Methylbutanoate, and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement

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Title A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-Methylbutanoate, and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement
 
Creator FERNANDES, RA
CHOWDHURY, AK
 
Subject Natural products
Total synthesis
Rearrangement
Terpenoids
Pheromones
PINK HIBISCUS MEALYBUG
SEX-PHEROMONE
PLANOCOCCUS-FICUS
ENANTIOSELECTIVE SYNTHESIS
MACONELLICOCCUS-HIRSUTUS
AGGREGATION PHEROMONE
RACEMIC LAVANDULOL
ALLYLIC ALCOHOLS
VINE MEALYBUG
ACID
 
Description An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-16T14:07:21Z
2014-10-16T14:07:21Z
2013
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013(23)5165-5170
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201300520
http://dspace.library.iitb.ac.in/jspui/handle/100/15743
 
Language en