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Pericyclic Reactions: Cycloadditions and Diels-Alder Reaction

Cycloadditions: Natural Products by Diels-Alder Reaction

As a C-C bond-forming reaction with high stereoselectivity (see also Stereochemistry of Cycloadditions), the Diels-Alder reaction represents one of the most important methodologies in synthetic chemistry. The following steroid synthesis involves the simultaneous formation in one step of two stereo centers and three rings.

Steroid synthesis by Diels-Alder reaction

Estradiol and estrone are estrogens or female sex hormones. In numerous other natural product syntheses, the Diels-Alder reaction is being used as a key step in the formation of the carbon skeleton.

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