Retrosynthetic Analysis and the Diels-Alder Reaction

Diels-Alder reactions are widely used for making carbon-carbon bonds, and retrosynthetic analysis can reveal opportunities for their application. If a synthetic target contains a cyclohexene ring, start with the double bond and use curved arrows to disconnect the bonds to be formed in the sought-for cycloaddition. For example  

In deciding whether the cycloaddition revealed by the disconnection is feasible or not, examine the aUcene to make sure that it is a reactive dienophile. Usually this means that the double bond bears an electron-attracting group, especially C=0 or C=N. 

What diene and dienophile could you use to prepare the compound shown  

The number of reaction types that we have covered to this point is extensive enough to allow the construction of relatively complicated products from simple, readily available starting materials. Thus, recognizing that the bicyclo[2.2.2]octene derivative shown is accessible by a Diels-Alder reaction leads us back to cyclohexanol as the source of six of its carbons. 

Write equations in the synthetic direction for the preparation of 5,6-dicyanobicycio[2.2.2]oct-2-ene from cyciohexanoi and any necessary organic or inorganic reagents. 

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