Rapid Access to Tetracyclic Core of Wortmannin via an Intramolecular Reductive Olefin Coupling Strategy.

A convergent approach to assemble the fused BCDE tetracyclic framework of wortmannin is presented. This route features a very challenging Suzuki-Miyaura coupling to prepare the fully functionalized furan intermediate, a Negishi-type acylation to unite the two enantio-enriched fragments, and a subsequent hydrogen-atom-transfer-initiated 6-endo radical cyclization to install the central cyclohexadienone moiety, which establishes the C10 all-carbon quaternary stereocenter.