Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

Nobuyuki Kawai; Yuko Fujibayashi; Seiya Kuwabara; Ken Ichi Takao; Yasuharu Ijuin; Susumu Kobayashi

doi:10.1016/S0040-4020(00)00619-0

Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

Nobuyuki Kawai, Yuko Fujibayashi, Seiya Kuwabara, Ken Ichi Takao, Yasuharu Ijuin, Susumu Kobayashi

Department of Applied Chemistry

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

30 Citations (Scopus)

Abstract

In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6467-6478
Number of pages	12
Journal	Tetrahedron
Volume	56
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(00)00619-0
Publication status	Published - 2000 Aug 25

Keywords

Akaterpin
Cis-decalin
Intramolecular Diels-Alder
Trans-decalin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00619-0

Cite this

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title = "Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC",

abstract = "In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.",

keywords = "Akaterpin, Cis-decalin, Intramolecular Diels-Alder, Trans-decalin",

author = "Nobuyuki Kawai and Yuko Fujibayashi and Seiya Kuwabara and Takao, {Ken Ichi} and Yasuharu Ijuin and Susumu Kobayashi",

note = "Funding Information: We thank Prof. Kazuo Umezawa (Keio University) for helpful discussions. We also thank Shin-Etsu Chemical Co. Ltd for a generous donation of silyl compounds. This work was supported in part by CREST, Japan Science and Technology Corporation.",

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doi = "10.1016/S0040-4020(00)00619-0",

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T1 - Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

AU - Kawai, Nobuyuki

AU - Fujibayashi, Yuko

AU - Kuwabara, Seiya

AU - Takao, Ken Ichi

AU - Ijuin, Yasuharu

AU - Kobayashi, Susumu

N1 - Funding Information: We thank Prof. Kazuo Umezawa (Keio University) for helpful discussions. We also thank Shin-Etsu Chemical Co. Ltd for a generous donation of silyl compounds. This work was supported in part by CREST, Japan Science and Technology Corporation.

PY - 2000/8/25

Y1 - 2000/8/25

N2 - In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.

AB - In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.

KW - Akaterpin

KW - Cis-decalin

KW - Intramolecular Diels-Alder

KW - Trans-decalin

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DO - 10.1016/S0040-4020(00)00619-0

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VL - 56

SP - 6467

EP - 6478

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

Abstract

Keywords

ASJC Scopus subject areas

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