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RCM/PCC oxidation strategy for synthesis of functionalized cyclic alpha,beta-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

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Title RCM/PCC oxidation strategy for synthesis of functionalized cyclic alpha,beta-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers
 
Creator SRIKANTH, GSC
KRISHNA, UM
TRIVEDI, GK
CANNON, JF
 
Subject goniothalamus-giganteus annonaceae
styryl-lactones
pyridinium chlorochromate
(+)-goniofufurone
(+)-goniotriol
8-acetylgoniotriol
(+)-goniopypyrone
(+)-altholactone
goniofufurone
ring
styryllactones
goniotriol
rcm and pcc oxidation
 
Description A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-26T05:59:15Z
2011-12-26T12:57:18Z
2011-12-27T05:47:24Z
2011-08-26T05:59:15Z
2011-12-26T12:57:18Z
2011-12-27T05:47:24Z
2006
 
Type Article
 
Identifier TETRAHEDRON, 62(48), 11165-11171
0040-4020
http://dx.doi.org/10.1016/j.tet.2006.09.016
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11216
http://hdl.handle.net/10054/11216
 
Language en