Q.34. - Organic Chemistry

Question

Question: What product is formed when a solution of A and B is treated with mild base? This reaction is the first step in the synthesis of rosuvastatin (sold as a calcium salt under the trade name Crestor), a drug used to treat patients with high cholesterol.

Step-by-Step Solution

Answer

Answer

The product of the reaction is given hereunder.

Step 1: Aldol reaction

In the presence of a mild base, the aldol reaction takes place in between the two carbonyl compounds. As a result, an additional C-C bond is formed between the two compounds.

Step 2: Intramolecular proton transfer

In case there is a carbocation or carbanion generation in the intermediate, an intramolecular hydrogen shift takes place to achieve increased stability. 

Step 3: Product of the given reaction

The product of the given reaction is given hereunder.