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.
| Original language | English |
|---|---|
| Pages (from-to) | 6083-6086 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 34 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - 1993 Sep 17 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
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. / Maki, Shojiro; Kosemura, Seiji; Yamamura, Shosuke; Ohba, Shigeru.
In: Tetrahedron Letters, Vol. 34, No. 38, 17.09.1993, p. 6083-6086.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=0027451960&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0027451960&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)61734-3
DO - 10.1016/S0040-4039(00)61734-3
M3 - Article
AN - SCOPUS:0027451960
VL - 34
SP - 6083
EP - 6086
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 38
ER -