Question

What two carbonyl compounds are required for the synthesis of morachalcone A (the aromatase inhibitor discussed in the box below), via a Claisen–Schmidt condensation?

Short answer

The product followed as:

Step-by-step solution

Claisen-Schmidt condensation

It is also known as cross aldol condensation in which the condensation reaction of aldehyde and carbonyl occurs and the formation of $\mathbf{\beta }$-hydroxyl carbonyl compounds is followed by the nucleophilic attack on enolate ion.

Carbonyl compound of morachalcone A

The carbonyl product is condensed to form the morachalcone A and we can identify the two-carbonyl compound from their structure by breaking the double bond two compounds are formed named 2,4 dihydroxy benzaldehyde and 1(2,4-dihydroxy)3-(3-methylbut-2-ene -yl) phenyl) ethenone.

Product formation

Synthesis of morachalcone A

1. The carbonyl compound with alpha carbon reacts with the base leading to the abstraction of the proton.

2. Carbonyl having no alpha carbon acts as a nucleophile and attacks on enolate of another carbonyl compound.

3. Followed by loss of water

4. Formation of the double bond

5. Condensation product morachaclone A obtained

Formation of morachaclone A