Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain

Shojiro Maki; Seiji Kosemura; Shosuke Yamamura; Shigeru Ohba

doi:10.1016/S0040-4039(00)61734-3

Facile synthesis of tricyclo[5.4.0.0^1,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain

Shojiro Maki, Seiji Kosemura, Shosuke Yamamura, Shigeru Ohba

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

13 Citations (Scopus)

Abstract

3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing ⁿBu₄NBF₄ to afford a tricyclo[5.3.1.0^1,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.0^1,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.0^1,5]undec-9-ene-8,11-diones were also obtained in good yields.

Original language	English
Pages (from-to)	6083-6086
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(00)61734-3
Publication status	Published - 1993 Sep 17

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{78b37136f3d647488edca79be0ff10ff,

title = "Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain",

abstract = "3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.",

author = "Shojiro Maki and Seiji Kosemura and Shosuke Yamamura and Shigeru Ohba",

year = "1993",

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language = "English",

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pages = "6083--6086",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain

AU - Maki, Shojiro

AU - Kosemura, Seiji

AU - Yamamura, Shosuke

AU - Ohba, Shigeru

PY - 1993/9/17

Y1 - 1993/9/17

N2 - 3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.

AB - 3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.

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EP - 6086

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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