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

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

doi:10.1021/acs.joc.7b02997

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

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

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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 language	English
Pages (from-to)	7010-7018
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	83
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.7b02997
Publication status	Published - 2018 Jul 6

ASJC Scopus subject areas

Organic Chemistry

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

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.",

author = "Kuniaki Tatsuta and Daisuke Sekine and Shinichi Hayama and Yasuhiro Kataoka and Shinya Hayashi and Seijiro Hosokawa",

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AU - Tatsuta, Kuniaki

AU - Sekine, Daisuke

AU - Hayama, Shinichi

AU - Kataoka, Yasuhiro

AU - Hayashi, Shinya

AU - Hosokawa, Seijiro

PY - 2018/7/6

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

Abstract

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