Keywords
(methylenedioxy)benzaldehyde
allylbenzenes
Baeyer–Villiger rearrangement
coenzyme Q
formylation
oxidation.
polyalkoxyquinone
Abstract
A general synthetic access to methoxy analogues of coenzymes Q bearing functional substituents with various chain lengths at the quinone ring was developed using available natural (polymethoxy)(methylenedioxy)allylbenzenes. The Baeyer-Villiger rearrangement of (methylenedioxy)benzaldehydes into phenols followed by facile oxidation to quinones with the methylenedioxy moiety opening was identified as the key step in the synthesis of the target 1,4- and 1,2-polyalkoxyquinones
References
.
Polyakova S.K., Balashova T.V., Rumyantcev R.V., Arsenyev M.V., Fukin G.K., Chesnokov S.A.
Mendeleev Communications,
2021
.
Wellington K.W.
RSC Advances,
2015
.
Matsumoto M., Kobayashi K., Hotta Y.
Journal of Organic Chemistry,
1984
.
Semenov V.V., Rusak V.V., Chartov E.M., Zaretskii M.I., Konyushkin L.D., Firgang S.I., Chizhov A.O., Elkin V.V., Latin N.N., Bonashek V.M., Stas’eva O.N.
Russian Chemical Bulletin,
2007
.
Samet A.V., Shevchenko O.G., Rusak V.V., Chartov E.M., Myshlyavtsev A.B., Rusanov D.A., Semenova M.N., Semenov V.V.
Journal of Natural Products,
2019
.
Asakawa T., Sagara H., Kanakogi M., Hiza A., Tsukaguchi Y., Ogawa T., Nakayama M., Ouchi H., Inai M., Kan T.
Organic Process Research and Development,
2019
.
Chen X., Gao M., Jian R., Hong W.D., Tang X., Li Y., Zhao D., Zhang K., Chen W., Zheng X., Sheng Z., Wu P.
Journal of Enzyme Inhibition and Medicinal Chemistry,
2020
.
Bowman C.M., Wikholm R.J., Boler J., Bogentoft C.B., Folkers K.
Journal of Medicinal Chemistry,
1973
.
Bogentoft C., Von Klaudy A., Folkers K.
Journal of Medicinal Chemistry,
1972
.
Coenzyme Q. 124. New substituted 2,3-dimethoxy-1,4-benzoquinones as inhibitors of coenzyme Q systems
Folkers K., Catlin J.C., Daves G.D.
Journal of Medicinal Chemistry,
1971
.
THE STRUCTURES OF OHCHINOLIDE A AND B, TWO NEW LIMONOIDS FROMMELIA AZEDARACHLINN.VAR. JAPONICAMAKINO
Ochi M., Kotsuki H., Ido M., Nakai H., Shiro M., Tokoroyama T.
Chemistry Letters,
1979
.
Yang H., Thiyagarajan V., Shen P., Mathew D.C., Lin K., Liao J., Hseu Y.
Journal of Experimental and Clinical Cancer Research,
2019
.
Hseu Y., Tsai T., Korivi M., Liu J., Chen H., Lin C., Shen Y., Yang H.
Scientific Reports,
2017
.
Dallacker F.
Monatshefte fur Chemie,
1969
.
Capon R.J., Ghisalberti E.L., Jefferies P.R.
Phytochemistry,
1981
.
Semenov V.V., Lichitsky B.V., Komogortsev A.N., Dudinov A.A., Krayushkin M.M., Konyushkin L.D., Atamanenko O.P., Karmanova I.B., Strelenko Y.A., Shor B., Semenova M.N., Kiselyov A.S.
European Journal of Medicinal Chemistry,
2017
.
Tsyganov D.V., Chernysheva N.B., Salamandra L.K., Konyushkin L.D., Atamanenko O.P., Semenova M.N., Semenov V.V.
Mendeleev Communications,
2013
.
Hseu Y., Thiyagarajan V., Tsou H., Lin K., Chen H., Lin C., Liao J., Yang H.
Oncotarget,
2016