Record Details

Chiral vicinal diols as platforms for separable diastereomers in Johnson-Claisen rearrangement: a new short route to (-)-nor-canadensolide, (-)-canadensolide and (-)-sporothriolide

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Chiral vicinal diols as platforms for separable diastereomers in Johnson-Claisen rearrangement: a new short route to (-)-nor-canadensolide, (-)-canadensolide and (-)-sporothriolide
 
Creator FERNANDES, RA
INGLE, AB
 
Subject enantioselective synthesis
formal synthesis
asymmetric dihydroxylation
stereoselective synthesis
efficient synthesis
diacetone glucose
allylic alcohols
gamma-lactones
canadensolide
sporothriolide
asymmetric synthesis
chiral vicinal diols
johnson-claisen rearrangement
nor-canadensolide
canadensolide
sporothriolide
 
Description The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-23T19:10:59Z
2011-12-26T12:56:34Z
2011-12-27T05:45:28Z
2011-08-23T19:10:59Z
2011-12-26T12:56:34Z
2011-12-27T05:45:28Z
2009
 
Type Article
 
Identifier TETRAHEDRON LETTERS, 50(10), 1122-1124
0040-4039
http://dx.doi.org/10.1016/j.tetlet.2008.12.084
http://dspace.library.iitb.ac.in/xmlui/handle/10054/10616
http://hdl.handle.net/10054/10616
 
Language en