Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC

Hayato Hosoi; Nobuyuki Kawai; Hideki Hagiwara; Takahiro Suzuki; Atsuo Nakazaki; Ken Ichi Takao; Kazuo Umezawa; Susumu Kobayashi

doi:10.1016/j.tetlet.2011.07.079

Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC

Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken Ichi Takao, Kazuo Umezawa, Susumu Kobayashi

研究成果: Article › 査読

5 被引用数 (Scopus)

抄録

We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1′ position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin.

本文言語	English
ページ（範囲）	4961-4964
ページ数	4
ジャーナル	Tetrahedron Letters
巻	52
号	38
DOI	https://doi.org/10.1016/j.tetlet.2011.07.079
出版ステータス	Published - 2011 9 21
外部発表	はい

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

文献へのアクセス

10.1016/j.tetlet.2011.07.079

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引用スタイル

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abstract = "We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1′ position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin.",

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AU - Hosoi, Hayato

AU - Kawai, Nobuyuki

AU - Hagiwara, Hideki

AU - Suzuki, Takahiro

AU - Nakazaki, Atsuo

AU - Takao, Ken Ichi

AU - Umezawa, Kazuo

AU - Kobayashi, Susumu

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N2 - We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1′ position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin.

AB - We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1′ position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin.

KW - Diastereoselective Diels-Alder reaction

KW - PI-PLC inhibitor

KW - Structure determination

KW - Total synthesis

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