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Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid

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Title Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
 
Creator FERNANDES, RA
HALLE, MB
CHOWDHURY, AK
INGLE, AB
 
Subject SUBSTITUTED PARACONIC ACIDS
DL-PROTOLICHESTERINIC ACID
CLAISEN REARRANGEMENT
CETRARIA-ISLANDICA
ENANTIOSELECTIVE SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
LICHENIC SUBSTANCES
NEPHROSTERINIC ACID
ALLYLIC ALCOHOLS
CROSS-METATHESIS
 
Description A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. (C) 2012 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T14:06:21Z
2014-10-16T14:06:21Z
2012
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY, 23(1)60-66
http://dx.doi.org/10.1016/j.tetasy.2011.12.012
http://dspace.library.iitb.ac.in/jspui/handle/100/15741
 
Language en