Synthesis of 2-acetylbicyclo [2.2. 1] hept-2-ene

LAM Cornelius, RGA Bone, RH Hastings…

Index: Cornelius, Lyndon A. M.; Bone, Richard G. A.; Hastings, Riley H.; Deardorff, Matthew A.; Scharlach, Randall A.; et al. Journal of Organic Chemistry, 1993 , vol. 58, # 11 p. 3188 - 3190

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Citation Number: 6

Abstract

I of this simple compound has been reported: and that involves a Diels-Alder cycloaddition of cyclopentadiene with 4-(benzyloxy)-3-buten-2-one followed by hydrogenation and dehydration. This provides the target molecule in 48% overall yield. Unfortunately, extension of this direct synthesis to less reactive nitrogen-containing dienes such as substituted pyrroles in place of cyclopentadiene is not possible. Another straightforward preparation ...