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...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-07, Vol.83 (13), p.7010-7018
Main Authors: Tatsuta, Kuniaki, Sekine, Daisuke, Hayama, Shinichi, Kataoka, Yasuhiro, Hayashi, Shinya, Hosokawa, Seijiro
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02997