American Chemical Society
jo7b02997_si_003.cif (258.68 kB)

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

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posted on 2018-01-16, 00:00 authored by Kuniaki Tatsuta, Daisuke Sekine, Shinichi Hayama, Yasuhiro Kataoka, Shinya Hayashi, Seijiro Hosokawa
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.