Synthesis of a Novel Taxa-Oxa-Sugar Hybrid Core Structure by Tandem Cross-Enyne Metathesis/IMDA
DSpace at IIT Bombay
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Title |
Synthesis of a Novel Taxa-Oxa-Sugar Hybrid Core Structure by Tandem Cross-Enyne Metathesis/IMDA
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Creator |
NANDURDIKAR, RS
SUBRAHMANYAM, AV KALIAPPAN, KP |
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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 |
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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.
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Publisher |
WILEY-V C H VERLAG GMBH
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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 |
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Type |
Article
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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 |
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Language |
en
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