A concise route to the C2-symmetric tricyclic skeleton of ryanodine

Ryanodine is a potent calcium channel modulator. In this Letter, we report the 10-step synthesis of the highly substituted tricyclic ring system of ryanodine. Diels–Alder reaction via dearomatization of 2,5-dimethylbenzene-1,4-diol and subsequent SmI2-mediated reductive coupling of eight-membered 1,5-diketone efficiently introduced the four consecutive fully substituted carbons of the tricyclo[3.3.2.02,6]decane system.