The total syntheses of salvia terpenes: (+)-grandione, (–)-brussonol, (–)-salviasperanol and (+)-salvadione-B
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By using an A + C → ABC cyclialkylation strategy we synthesized the icetexane-based diterpenes (–)-barbatusol, (+)-demethylsalvicanol, and (–)-brussonol. Synthetic (+)-demethylsalvicanol was dimerized to produce (+)-grandione using aqueous Diels–Alder conditions. A modification of our cyclialkylation strategy was used to construct the tricyclic skeleton of (–)-salviasperanol. Our synthesis of (+)-salvadione-B featured a regio- and stereospecific Diels–Alder reaction as well as an efficient oxidative free radical cyclization.