Intramolecular Diels–Alder cycloaddition

In organic chemistry, an intramolecular Diels-Alder cycloaddition is a Diels–Alder reaction in which the diene and the dienophile are both part of the same molecule.

[2] Because the two reacting groups are already attached, two basic modes of addition are possible in this reaction.

Depending on whether the tether that links to the dienophile is attached to the end or the middle of the diene, fused or bridged polycyclic ring systems can be formed.

[3] The tether than attaches the two reacting groups also affects the geometry of the reaction.

The following potential drugs have been synthesized using the intramolecular Diels-Alder reaction: salvinorin A,[7] himbacine,[8] and solanapyrone A.