Salvinorin A (1) was isolated from the leaves of Salvia divinorum, a Mexican medicinal plant also used for shamanic practices. The diterpene 1 is the most potent naturally occurring hallucinogen in humans known to date and a potent as well as highly selective κ-opioid receptor agonist. We have recently completed a concise total synthesis of 1 from 3-furaldehyde (3) via the bicyclic lactone 2 using two highly diastereoselective intramolecular Diels-Alder reactions (IMDA) as the key transformations.

Total synthesis of the neoclerodane diterpene salvinorin A via an intramolecular Diels-Alder strategy

256th National Meeting (2018)

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