TY - JOUR
T1 - Total Synthesis and Structural Determination of XR774, a Tyrosine Kinase Inhibitor
AU - Tatsuta, Kuniaki
AU - Sekine, Daisuke
AU - Hayama, Shinichi
AU - Kataoka, Yasuhiro
AU - Hayashi, Shinya
AU - Hosokawa, Seijiro
PY - 2018/7/6
Y1 - 2018/7/6
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.7b02997
DO - 10.1021/acs.joc.7b02997
M3 - Article
C2 - 29338228
AN - SCOPUS:85049607022
SN - 0022-3263
VL - 83
SP - 7010
EP - 7018
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -