TfOH catalysed domino-double annulation of arenes with propargylic alcohols: a unified approach to indene polycyclic systems.

The design and development of a TfOH catalysed domino strategy for the double annulation of arenes with propargylic alcohols for the rapid generation of indene based polycyclic systems is reported. The dehydration, intramolecular 6-endo-dig hydroarylation, and cationic cyclization were consecutively promoted by TfOH. The key features of this strategy are the formation of two C-C bonds, unified access to indene polycyclic systems, excellent yields (up to 95%), high atom economy (>90%), an operationally simple procedure, and water being the only byproduct. By extending this strategy, a two-step synthesis of the pentacyclic systems of hypoxylonol A (43% overall yield from α-tetralone), daldinone A (63% overall yield from β-tetralone) and spiro-tetracyclic framework of incarviatone A has also been achieved.