Stereoselective Synthesis of the Benzodihydropentalene Core of the Fijiolides

An efficient stereoselective synthesis of the enantiomer of the benzodihydropentalene core of fijiolides A and B has been achieved. The asymmetric conjugate addition of styrylboronic acid to an indenone produced the first stereocenter. Ring C was installed by ring-closing metathesis of a cis disubstituted indanone. Regioselective epoxide opening by NaSePh and subsequent oxidative elimination produced an allylic alcohol. The final introduction of the cyclopentadiene was possible by elimination of an in situ formed triflate.