(a) Write a reaction involving a lithium enolate for introduction of the methyl group in

Chapter 18, Problem 18.6

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(a) Write a reaction involving a lithium enolate for introduction of the methyl group in the following compound (an intermediate in a synthesis by E. J. Corey of cafestol, an anti-inflammatory agent found in coffee beans): O O (b) Dienolates can be formed from b-keto esters using two equivalents of LDA. The dienolate can then be alkylated selectively at the more basic of the two enolate carbons. Write a reaction for synthesis of the following compound using a dienolate and the appropriate alkyl halide:

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