Issue 13, 2006
From the journal:

Organic & Biomolecular Chemistry

Synthesis of tetrahydroxy perhydroaza-azulenes: tandem Johnson–Claisen rearrangement of d-glucose-derived allylic alcohols†

Shankar D. Markad,a   Narayan S. Karanjule,a   Tarun Sharma,b   Sushma G. Sabharwal,b   Vedavati G. Puranikc  and  Dilip D. Dhavale*a  

* Corresponding authors

a Garware Research Centre, Department of Chemistry, University of Pune, Pune, India
E-mail: ddd@chem.unipune.ernet.in

b Division of Biochemistry, Department of Chemistry, University of Pune, Pune, India

c Centre for Material Characterization, National Chemical Laboratory, Pune, India

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.

Graphical abstract: Synthesis of tetrahydroxy perhydroaza-azulenes: tandem Johnson–Claisen rearrangement of d-glucose-derived allylic alcohols

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Article information

DOI
https://doi.org/10.1039/B603545K
Article type
Paper
Submitted
08 Mar 2006
Accepted
09 May 2006
First published
25 May 2006

Org. Biomol. Chem., 2006,4, 2549-2555

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

S. D. Markad, N. S. Karanjule, T. Sharma, S. G. Sabharwal, V. G. Puranik and D. D. Dhavale, Org. Biomol. Chem., 2006, 4, 2549 DOI: 10.1039/B603545K

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