Diels–Alder Reactions of Masked o‐Benzoquinones with 1‐Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton
- 9 May 2014
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2014 (18) , 3794-3801
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.Keywords
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