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Synthesis 2004(8): 1150-1154  
DOI: 10.1055/s-2004-822352
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Chiral cis-Annulated Polycyclic Heterocycles from d-Glucose by Domino Knoevenagel-Hetero-Diels-Alder Reaction [1]

Gowravaram Sabitha*a, E. Venkata Reddya, Narjis Fatimaa, J. S. Yadava, K. V. S. Rama Krishnab, A. C. Kunwarb
a Organic Chemical Sciences, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
b NMR Group, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: Sabitha@iict.ap.nic.in;
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Publication History

Received 12 September 2003
Publication Date:
28 April 2004 (online)

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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.

Keywords

domino reaction - Knoevenagel reaction - Diels-Alder reaction - EDDA - diastereoselective

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IICT Communication No 030124.

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IICT Communication No 030124.