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

Kuniaki Tatsuta, Daisuke Sekine, Shinichi Hayama, Yasuhiro Kataoka, Shinya Hayashi, Seijiro Hosokawa

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)7010-7018
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number13
DOIs
Publication statusPublished - 2018 Jul 6

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Protein-Tyrosine Kinases
Tetralones
Nickel
XR774
benzo(j)fluoranthene
allyl alcohol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total Synthesis and Structural Determination of XR774, a Tyrosine Kinase Inhibitor. / Tatsuta, Kuniaki; Sekine, Daisuke; Hayama, Shinichi; Kataoka, Yasuhiro; Hayashi, Shinya; Hosokawa, Seijiro.

In: Journal of Organic Chemistry, Vol. 83, No. 13, 06.07.2018, p. 7010-7018.

Research output: Contribution to journalArticle

Tatsuta, Kuniaki ; Sekine, Daisuke ; Hayama, Shinichi ; Kataoka, Yasuhiro ; Hayashi, Shinya ; Hosokawa, Seijiro. / Total Synthesis and Structural Determination of XR774, a Tyrosine Kinase Inhibitor. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 13. pp. 7010-7018.
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