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Chapter 23: Q27. (page 924)

Question: Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Brforms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from thejack-o鈥�-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?

Short Answer

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Answer

The structure of X is shown as follows:

Step by step solution

01

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 伪 - 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.

02

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

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Most popular questions from this chapter

Question: Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an 伪-methylene- 纬-butyrolactone. This heterocyclic ring system is present in some antitumor agents.

Question:Explain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis.

Question: Draw the products formed (including stereoisomers) in each reaction.

Question: Draw the products obtained (including stereochemistry) when each compound is treated with LDA, followed by CH3l.

Question:What cyclic product is formed from each dihalide using the malonic ester synthesis?
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