A stereoselective intramolecular Diels–Alder strategy for the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes

A stereoselective Lewis acid-catalyzed and chelation controlled intramolecular Diels–Alder entry into the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes is described. The approach affords an efficient, high yield, access to aromatic C-ring taxanes variably functionalized at the C2, C4, C5, and C9 positions.