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

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

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4961-4964
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2011.07.079
Publication status	Published - 2011 Sept 21
Externally published	Yes

Keywords

Diastereoselective Diels-Alder reaction
PI-PLC inhibitor
Structure determination
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.07.079

Cite this

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

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.",

keywords = "Diastereoselective Diels-Alder reaction, PI-PLC inhibitor, Structure determination, Total synthesis",

author = "Hayato Hosoi and Nobuyuki Kawai and Hideki Hagiwara and Takahiro Suzuki and Atsuo Nakazaki and Takao, \{Ken Ichi\} and Kazuo Umezawa and Susumu Kobayashi",

note = "Funding Information: This research was supported in part by a Grant-in-Aid for Scientific Research (B) (KAKENHI No. 22390004 ) from the Japan Society for the Promotion of Science . Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2011.07.079",

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volume = "52",

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journal = "Tetrahedron Letters",

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T1 - Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC

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

N1 - Funding Information: This research was supported in part by a Grant-in-Aid for Scientific Research (B) (KAKENHI No. 22390004 ) from the Japan Society for the Promotion of Science . Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

PY - 2011/9/21

Y1 - 2011/9/21

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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DO - 10.1016/j.tetlet.2011.07.079

M3 - Article

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SN - 0040-4039

VL - 52

SP - 4961

EP - 4964

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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