First apply Birch reduction: the methoxy substituent is electron donating, so the methoxy-bearing carbon remains in an unsaturated part of the reduced ring. Next, one equivalent of ozone cleaves the more electron-rich enol-ether double bond. Work-up converts its methoxy-bearing end to a methyl ester and its alkyl-bearing end to a ketone, while the other double bond remains. Tracking the Et and Me substituents gives the ester–ketone alkene drawn in C, including its retained alkene geometry.
More Reduction: Catalytic homogeneous and heterogeneous hydrogenation. Metal based reductions using Li/Na in liquid ammonia, magnesium, zinc, titanium, and samarium. Hydride transfer reagents: NaBH4, L-selectride, K-selectride, Luche reduction, LiAlH4 and DIBAL-H. questions
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