Volume 20, Issue 22
Heterocyclic Compounds
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ChemInform Abstract: Reactions of α- and β-Acylated Furans with Conjugated Dienes.

E. WENKERT

E. WENKERT

Dep. Chem., Univ. Calif., San Diego, La Jolla, CA 92093, USA

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S. R. PIETTRE

S. R. PIETTRE

Dep. Chem., Univ. Calif., San Diego, La Jolla, CA 92093, USA

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First published: May 30, 1989

Abstract

Diels-Alder reaction of the 1,3-butadienes (I) and (V) with methyl furoate (II) gives only poor yields of cycloadducts.

ChemInform Abstract

Diels-Alder reaction of the 1,3-butadienes (I) and (V) with methyl furoate (II) gives only poor yields of cycloadducts. Furfural (IX) and isoprene (V) form the heteroene products (X) and (XI). The cycloaddition of (V) with 3-formylbenzofuran (XII) is also studied. Diels-Alder reaction of the butadiene (XIV) with dimethyl 2,4-furandicarboxylate (XV), followed by deprotection, yields the keto ester (XVI), a potential precursor of prephenic acid (XVII).

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