Volume 24, Issue 30
Natural Products
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ChemInform Abstract: Diels-Alder Reactions with an α,β-Unsaturated Aldehyo Sugar. A Route to 6-Oxabicyclo(3.2.1)octanes.

E. R. GALAN

E. R. GALAN

Dep. Quim. Org., Fac. Cienc., Univ. Extremadura, 06071 Badajoz, Spain

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M. J. CHAMIZO

M. J. CHAMIZO

Dep. Quim. Org., Fac. Cienc., Univ. Extremadura, 06071 Badajoz, Spain

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J. A. SERRANO

J. A. SERRANO

Dep. Quim. Org., Fac. Cienc., Univ. Extremadura, 06071 Badajoz, Spain

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First published: July 27, 1993

Abstract

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ChemInform Abstract

Diels-Alder reaction of the sugar (I) with the diene (II) produces a mixture of the cyclohexenes (IIIa) and (IVa). The derivatives (IIIc) and (IVc), obtained via reduction and acetylation, give the bridged title systems (V) and (VI) (yields not given) upon acidic treatment. The method represents a short approach to this class of compounds in a stereocontrolled manner.

chemical structure image

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