Rapid construction of polycyclic ring systems from aromatics: stereoselective synthesis of the carbon framework of vinigrol

The stereoselective syntheses of the tricyclic core structure of vinigrol and highly functionalized polycyclic molecules from 5-bromo-2-methoxyphenol in five synthetic steps are reported. Intramolecular and intermolecular Diels–Alder reactions and tandem oxy-Cope/ene reactions are the key steps in the synthesis.