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- Title
Diels-Alder Reactions of Masked o-Benzoquinones with 1-Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton.
- Authors
Niu, Guang‐Hao; Hou, Chieh‐Shen; Chuang, Gary Jing; Wu, Chi‐Phi; Liao, Chun‐Chen
- 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]octenones could be transformed into the corresponding decahydrophenanthrenes through a Cope rearrangement at 220 °C. Thus, these tandem reactions provide a short and efficient entry to the decahydrophenanthrene skeleton from easily available 2-methoxyphenols.
- Subjects
BENZOQUINONES; DIELS-Alder reaction; VINYLCYCLOHEXENE; RING formation (Chemistry); PHENANTHRENE; CYCLOOCTENONE; GUAIACOL
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 18, p3794
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201400016