Search

The synthesis of compound 11 , which features a diene moiety bearing electron withdrawing groups at the 1 and 3 positions, and its completely regioselective inverse electron demand Diels-Alder reactions with 1,1-diethoxyethylene, ethyl vinyl ether and styrene are described. Endo addition is preferred. The direct synthetic precursor of 11 , in which one of the electron withdrawing groups (a ketone) is protected, participates in normal electron demand Diels-Alder reactions with 1,4-naphthoquinone and N -phenylmaleimide, but is unreactive towards 1,1-diethoxyethylene.