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

ASJC Scopus subject areas

  • Organic Chemistry

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