Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

Nobuyuki Kawai; Ken ichi Takao; Susumu Kobayashi

doi:10.1016/S0040-4039(99)00686-3

Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

Nobuyuki Kawai, Ken ichi Takao, Susumu Kobayashi

Department of Applied Chemistry

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

15 Citations (Scopus)

Abstract

In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure.

Original language	English
Pages (from-to)	4193-4196
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4039(99)00686-3
Publication status	Published - 1999 May 28

Keywords

Akaterpin
Cis-decalin
Intramolecular Diels-Alder reaction
Reductive alkylation
Trans-decalin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00686-3

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title = "Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone",

abstract = "In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure.",

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

author = "Nobuyuki Kawai and Takao, {Ken ichi} and Susumu Kobayashi",

note = "Funding Information: Acknowledgment: 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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T1 - Synthetic study of akaterpin

T2 - Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

AU - Kawai, Nobuyuki

AU - Takao, Ken ichi

AU - Kobayashi, Susumu

N1 - Funding Information: Acknowledgment: 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 - 1999/5/28

Y1 - 1999/5/28

N2 - In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure.

AB - In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure.

KW - Akaterpin

KW - Cis-decalin

KW - Intramolecular Diels-Alder reaction

KW - Reductive alkylation

KW - Trans-decalin

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 22

ER -

Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

Abstract

Keywords

ASJC Scopus subject areas

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