The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: an efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors

Chaudhari, Vinod D. ; Ajish Kumar, K. S. ; Dhavale, Dilip D. (2004) The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: an efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors Tetrahedron Letters, 45 (45). pp. 8363-8366. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2004.09.053

Abstract

A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-D-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from D-glucose, as the key step.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Alkaloids; Pyrrolidines; Enzyme Inhibitors; Carbohydrate Mimetics
ID Code:9568
Deposited On:02 Nov 2010 11:55
Last Modified:31 May 2011 11:55

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