Markad, Shankar D. ; Karanjule, Narayan S. ; Sharma, Tarun ; Sabharwal, Sushma G. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2006) Synthesis of tetrahydroxy perhydroaza-azulenes: tandem Johnson-Claisen rearrangement of D-glucose-derived allylic alcohols Organic and Biomolecular Chemistry, 4 (13). pp. 2549-2555. ISSN 1477-0520
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Official URL: http://pubs.rsc.org/en/content/articlelanding/2006...
Related URL: http://dx.doi.org/10.1039/B603545K
Abstract
The Johnson-Claisen rearrangement of D-glucose-derived allylic alcohols 5a,b afforded sugar-substituted γ,δ-unsaturated ester 6 in high yield. Conversion of the ester group to an azidomethyl group, epoxidation of the double bond and hydrogenation gave pyrrolidine ring skeletons 13a and 13b, which were transformed to tetrahydroxy perhydroaza-azulenes 1a and 1b, respectively. Glycosidase inhibitory activity was also evaluated.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 75338 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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