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Synthesis of beta,gamma-disubstituted-gamma-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

DSpace at IIT Bombay

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Title Synthesis of beta,gamma-disubstituted-gamma-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
 
Creator FERNANDES, RA
INGLE, AB
CHAVAN, VP
 
Subject enantioselective synthesis
formal synthesis
asymmetric dihydroxylation
stereoselective synthesis
efficient synthesis
diacetone glucose
allylic alcohols
gamma-lactones
(-)-canadensolide
acid
 
Description The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-26T20:35:57Z
2011-12-26T12:57:35Z
2011-12-27T05:43:53Z
2011-08-26T20:35:57Z
2011-12-26T12:57:35Z
2011-12-27T05:43:53Z
2009
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY, 20(24), 2835-2844
0957-4166
http://dx.doi.org/10.1016/j.tetasy.2009.11.018
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11429
http://hdl.handle.net/10054/11429
 
Language en