Lecture Notes: Diels-Alder In Synthesis
The clue for a Diels-Alder disconnection is a cyclohexene ring having an electron-withdrawing group on the side of the ring opposite to the double bond.

Ester groups are trans in the D-A adduct so they must be trans in the dienophile
Ha & Hbare cis in the product because they were cis in the quinone dienophile

Hc is also cis to Ha & Hb because the D-A reaction is stereoselectively endo.
Since the D-A reaction is such a good synthetic tool, it is wourth going to some trouble to get back to a recognizable D-A product in your analysis.

Propose a synthesis of the target molecule that incorporates two Diels-Alder reactions.

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Last Modified February 1, 1998

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