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^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

4 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	7010-7018
ページ数	9
ジャーナル	Journal of Organic Chemistry
巻	83
号	13
DOI	https://doi.org/10.1021/acs.joc.7b02997
出版ステータス	Published - 2018 7月 6

ASJC Scopus subject areas

有機化学

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10.1021/acs.joc.7b02997

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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 - Sekine, Daisuke

AU - Hayama, Shinichi

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AU - Hayashi, Shinya

AU - Hosokawa, Seijiro

PY - 2018/7/6

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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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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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

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