Diels–Alder Reactions of Masked o??Benzoquinones with 1??Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton

GH Niu, CS Hou, GJ Chuang, CP Wu…

Index: Niu, Guang-Hao; Hou, Chieh-Shen; Chuang, Gary Jing; Wu, Chi-Phi; Liao, Chun-Chen European Journal of Organic Chemistry, 2014 , vol. 2014, # 18 p. 3794 - 3801

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Abstract

Abstract Masked o-benzoquinones (MOBs), which were generated in situ from 2- methoxyphenols, underwent Diels–Alder reactions with 1-vinylcyclohexenes to produce the corresponding cycloaddition products, that is, decahydrophenanthrenes along with bicyclo [2.2. 2] octenones. In the former case, the MOBs serve as the dienophile, and in the later case, the 1-vinylcyclohexenes act as the dienophile. The obtained bicyclo [2.2. 2] ...

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