Nandurdikar, Rahul S. ; Subrahmanyam, Ayyagari V. ; Kaliappan, Krishna P. (2010) Synthesis of a novel taxa-oxa-sugar hybrid core structure by tandem cross-enyne metathesis/IMDA European Journal of Organic Chemistry, 2010 (14). pp. 2788-2799. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.201000001
Abstract
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.
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
Keywords: | Antitumor Agents; Taxol; Eleutherobin; Hybrid Structure; Metathesis; Cycloaddition |
ID Code: | 104977 |
Deposited On: | 19 May 2017 10:24 |
Last Modified: | 19 May 2017 10:24 |
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