Total Synthesis and Structural Determination of XR774, a Tyrosine Kinase Inhibitor

Total synthesis and structural determination of XR774 has been accomplished. The benzo­[j]­fluoranthene skeleton has been constructed by regioselective coupling between tetraline 3 and tetralone 4 successively followed by the sequential transformation including the Birch reduction to prepare allylic alcohol, simultaneous bromination of vinylic and aromatic moieties, and the nickel-mediated intramolecular coupling reaction. The optical resolution of racemic 17 led to the first total synthesis of (−)-XR774.