Total Synthesis of (±)-11-O-Debenzoyltashironin

Significance: Danishefsky and co-workers report the first total synthesis of the sesquiterpene ()-11-O-debenzoyltashironin.The natural product, isolated from the pericaps of Illicium merrillianum, exhibits potent neurotrophic activity in fetal-rat cortical neurons.The synthesis relies in a remarkable tandem oxidative dearomatization/ transannular Diels-Alder reaction, which rapidly assembles the tetracyclic core of the target molecule.