Q27. - Organic Chemistry

Question

Question: Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH₂CH₂Br  forms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from thejack-o’-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?

Step-by-Step Solution

Answer

Answer

 

The structure of X is shown as follows:

Step 1: Acetoacetic ester synthesis

The acetoacetic ester synthesis is a method that converts ethyl acetoacetate into a ketone having one or two alkyl groups on the $\alpha$ - carbon.

It is a three-steps process where an acid-base reaction takes place first followed by alkylation, and the last step involves hydrolysis and deprotonation.

Step 2: Detailed stepwise mechanism for obtaining X

The reaction scheme deals with the intramolecular acetoacetic ester reaction where three to six-membered rings are formed.

 

Representation of product X