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A concise synthesis of paraconic acids: (-)-methylenolactocin and (-)-phaseolinic acid

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Title A concise synthesis of paraconic acids: (-)-methylenolactocin and (-)-phaseolinic acid
 
Creator FERNANDES, RA
CHOWDHURY, AK
 
Subject BUTYROLACTONE NATURAL-PRODUCTS
METHYLENE-GAMMA-BUTYROLACTONES
DL-PROTOLICHESTERINIC ACID
CHIRAL BUTENOLIDE SYNTHONS
RING-CLOSING METATHESIS
METAL RADICAL SOURCE
PI-ALLYL COMPLEXES
ONE-CARBON SOURCE
ENANTIOSELECTIVE SYNTHESIS
(+)-NEPHROSTERANIC ACID
 
Description A concise synthesis of (-)-methylenolactocin and (-)-phaseolinic acid, the common members of the paraconic acids, is described. The synthesis is based on regioselective asymmetric dihydroxylation and the orthoester Johnson-Claisen rearrangement of allyl alcohol with a vicinal diol functionality as the key steps. The synthesis was completed in 10 steps with overall yields of 4.1% for (-)-methylenolactocin and 4.3% for (-)-phaseolinic acid. (C) 2011 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2012-06-26T08:39:40Z
2012-06-26T08:39:40Z
2011
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY,22(10)1114-1119
0957-4166
http://dx.doi.org/10.1016/j.tetasy.2011.05.007
http://dspace.library.iitb.ac.in/jspui/handle/100/14204
 
Language English