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Synthesis 2004(8): 1150-1154
DOI: 10.1055/s-2004-822352
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]
Further Information
Received
12 September 2003
Publication Date:
28 April 2004 (online)
Publication History
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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References
IICT Communication No 030124.