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Synthesis of a Novel Taxa-Oxa-Sugar Hybrid Core Structure by Tandem Cross-Enyne Metathesis/IMDA

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Title Synthesis of a Novel Taxa-Oxa-Sugar Hybrid Core Structure by Tandem Cross-Enyne Metathesis/IMDA
 
Creator NANDURDIKAR, RS
SUBRAHMANYAM, AV
KALIAPPAN, KP
 
Subject ring-closing-metathesis
natural-product eleutherobin
dess-martin periodinane
olefin-metathesis
biological evaluation
organic-synthesis
antitumor agents
stereocontrolled synthesis
common pharmacophore
sarcodictyon-roseum
antitumor agents
taxol
eleutherobin
hybrid structure
metathesis
cycloaddition
 
Description This paper describes our design and efforts in synthesizing new scaffolds with taxol-eleutherobin hybrid core structures and a taxol-sugar hybrid. The synthesis of taxol-eleutherobin hybrids involved the synthesis of the A-ring fragment from carvone and the C-ring fragment from either D-mannose or D-glucose. The Shapiro reaction was used as the key reaction to couple the A- and C-ring fragments of these hybrid structures. Unfortunately, another key reaction (RCM) failed to form the B-ring and essentially the core unit. However, a tandem enyne cross-metathesis/intramolecular Diels-Alder strategy was utilized for the synthesis of a taxa-oxa-sugar hybrid.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2011-09-01T21:34:14Z
2011-12-26T12:59:48Z
2011-12-27T05:52:42Z
2011-09-01T21:34:14Z
2011-12-26T12:59:48Z
2011-12-27T05:52:42Z
2010
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (14), 2788-2799
1434-193X
http://dx.doi.org/10.1002/ejoc.201000001
http://dspace.library.iitb.ac.in/xmlui/handle/10054/12874
http://hdl.handle.net/10054/12874
 
Language en