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An extremely useful diene in the synthesis of many natural products is known as Danishefsky’s diene. This compound is useful because after the Diels–Alder reaction it can be converted into a product that could not be accessed by a typical Diels–Alder reaction. Show the Diels–Alder adduct and propose a mechanism that accounts for the final products.

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 14.SE, Problem 24MP
Textbook Problem
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An extremely useful diene in the synthesis of many natural products is known as Danishefsky’s diene. This compound is useful because after the Diels–Alder reaction it can be converted into a product that could not be accessed by a typical Diels–Alder reaction. Show the Diels–Alder adduct and propose a mechanism that accounts for the final products.

Chapter 14.SE, Problem 24MP, An extremely useful diene in the synthesis of many natural products is known as Danishefsky’s

Interpretation Introduction

Interpretation:

The structure of the Diels-Alder adduct formed in the reaction between Danishfsky’s diene with acrolein a mechanism that accounts for the formation of final products is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state.

To give:

The structure of the Diels-Alder adduct formed in the reaction between Danishfsky’s diene and acrolein with a mechanism that accounts for the formation of final products.

Explanation of Solution

In the first step Danishfsky’s diene reacts with the dinophile, acrolein through a six membered cyclic transition state to yield an...

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Chapter 14 Solutions

Organic Chemistry
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