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

Gowravaram Sabitha; E. Venkata Reddy; Narjis Fatima; J. S. Yadav; K. V. S. Rama Krishna; A. C. Kunwar

doi:10.1055/s-2004-822352

PAPER

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

Gowravaram Sabitha*^a, E. Venkata Reddy^a, Narjis Fatima^a, J. S. Yadav^a, K. V. S. Rama Krishna^b, A. C. Kunwar^b
^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;

Abstract

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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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References

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