Chapter 18, Problem 6PP

Practice Problem 18.6

(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):

(b) Dienolates can be formed from $\beta$ -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 ap-propriate alkyl halide: