Synthesis of tetrahydroxy perhydroaza-azulenes: tandem Johnson-Claisen rearrangement of D-glucose-derived allylic alcohols

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

Full text not available from this repository.

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

Repository Staff Only: item control page