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

J Org Chem

Department of Applied Chemistry, Faculty of Science and Engineering , Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 , Japan.

Published: July 2018

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.

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http://dx.doi.org/10.1021/acs.joc.7b02997DOI Listing

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