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Chapter 16: PROBLEM 16.75 (page 640)

Question: Devise a stepwise mechanism for the conversion of M to N. N has been converted in several steps to lysergic acid, a naturally occurring precursor of the hallucinogen LSD (Figure 18.4).

Short Answer

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Answer

Step by step solution

01

Retro Diels-Alder reaction

The retro Diels-Alder product may undergo ring-opening.

The driving force for the retro Diels-Alder product is the formation of another product by the cycloaddition or relaxation of the strained product.

02

Explanation

Compound M undergoes ring opening via the retro Diels Alder reaction and further undergoes intramolecular Diels-Alder reaction.

The reaction scheme is shown below:

Retro Diels-Alder product

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