Question

Question: Zingerone, a spicy-sweet component of cooked ginger, can be converted to its protected TBDMS ether A, as we learned in Chapter 20. How can A be converted to gingerol, a compound present in fresh ginger, using a directed aldol reaction as a key step?

Short answer

Answer

Step-by-step solution

Directed aldol reaction

The crossed aldol reaction, which clearly defines which carbonyl forms the enolate and which acts as the electrophile, is referred to as the directed aldol reaction.

Conversion of A to Gingerol

The conversion of compound A to Gingerol is shown below.

• Generation of enolate

Generation of enolate

• Attack of enolate on the carbonyl compound

Synthesis of Gingerol