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

応用化学科

研究成果: Article › 査読

31 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	6467-6478
ページ数	12
ジャーナル	Tetrahedron
巻	56
号	35
DOI	https://doi.org/10.1016/S0040-4020(00)00619-0
出版ステータス	Published - 2000 8月 25

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4020(00)00619-0

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引用スタイル

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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.",

year = "2000",

month = aug,

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

language = "English",

volume = "56",

pages = "6467--6478",

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issn = "0040-4020",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/0034714389

UR - https://www.scopus.com/pages/publications/0034714389#tab=citedBy

U2 - 10.1016/S0040-4020(00)00619-0

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

M3 - Article

AN - SCOPUS:0034714389

SN - 0040-4020

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

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