Volume 26, Issue 51
Natural Products
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ChemInform Abstract: Diels-Alder Reactions of Isoprene and 1,3-Butadiene with Nitroheptenes Derived from Sugars.

E. ROMAN

E. ROMAN

Dep. Quim. Org., Univ. Extremadura, E-06071 Badajoz, Spain

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M. BANOS

M. BANOS

Dep. Quim. Org., Univ. Extremadura, E-06071 Badajoz, Spain

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J. I. GUTIERREZ

J. I. GUTIERREZ

Dep. Quim. Org., Univ. Extremadura, E-06071 Badajoz, Spain

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J. A. SERRANO

J. A. SERRANO

Dep. Quim. Org., Univ. Extremadura, E-06071 Badajoz, Spain

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First published: December 19, 1995

Abstract

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ChemInform Abstract

The title reactions show an unlike stereoselectivity, as a consequence of the configuration of the adjacent chiral center to the dienophilic double bond. For isoprene adducts (III)-(VI), the favored regioisomers are those in which the nitro and the methyl groups on cyclohexene rings are in a 1,4-relationship. Treatment of (IIIa) with Bu3SnH/AIBN leads to the corresponding denitrated derivative.

chemical structure image

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