American Chemical Society
ol8b00163_si_001.pdf (4.44 MB)

Stereoselective Synthesis of the Benzo­dihydro­pentalene Core of the Fijiolides

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journal contribution
posted on 2018-02-16, 00:30 authored by Timon Kurzawa, Klaus Harms, Ulrich Koert
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.