Diastereoselective synthesis of chiral cis-annulated polycyclic heterocycles from D-glucose by domino Knoevenagel-hetero-Diels-Alder reaction

Sabitha, Gowravaram ; Venkata Reddy, E. ; Fatima, Narjis ; Yadav, J. S. ; Rama Krishna, K. V. S. ; Kunwar, A. C. (2004) Diastereoselective synthesis of chiral cis-annulated polycyclic heterocycles from D-glucose by domino Knoevenagel-hetero-Diels-Alder reaction Synthesis, 2004 (8). pp. 1150-1154. ISSN 0039-7881

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Official URL: http://www.thieme-connect.com/ejournals/abstract/s...

Related URL: http://dx.doi.org/10.1055/s-2004-822352

Abstract

A new and simple chiral synthesis of cis-annulated polycyclic dihydropyrans 4 and 8 has been achieved by domino Knoevenagel-hetero-Diels-Alder reactions of O-prenyl derivative of the chiral sugar derived aldehyde 2 with 1,3-dicarbonyl compounds 1 or 6 in MeCN in the presence of a catalytic amount of ethylenediammonium diacetate (EDDA). The products are formed with extremely high cis-selectivity in good to excellent yields.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Domino Reaction; Knoevenagel Reaction; Diels-Alder Reaction; EDDA; Diastereoselective
ID Code:63126
Deposited On:28 Sep 2011 03:21
Last Modified:28 Sep 2011 03:21

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