Abstract
Natural (5Z,9Z)-dienoic acids and key precursors of biologically active trienoic acids were prepared in high yields and with high stereoselectivity using cross-cyclomagnesiation of terminal and oxygenated 1,2-dienes with EtMgBr in the presence of Mg metal and Cp2TiCl2 catalyst at the key step.
References
1.
Carballeira N.M.
Progress in Lipid Research,
2008
2.
Djerassi C., Lam W.K.
Accounts of Chemical Research,
1991
3.
Egorova K.S., Seitkalieva M.M., Posvyatenko A.V., Khrustalev V.N., Ananikov V.P.
ACS Medicinal Chemistry Letters,
2015
4.
10.1016/j.mencom.2017.05.005_bib0020
Murakami
Res. Commun. Mol. Pathol. Pharmacol.,
1994
5.
Suzuki K., Nagao K., Tokunaga J., Katayama N., Uyeda M.
Journal of Enzyme Inhibition,
1996
6.
Carballeira N.M., Reyes E.D., Sostre A., Rodríguez A.D., Rodríguez J.L., González F.A.
Journal of Natural Products,
1997
7.
Kawashima H., Ohnishi M.
Lipids,
2015
8.
Adrian J., Stark C.B.
European Journal of Organic Chemistry,
2016
9.
D’yakonov V., Dzhemileva L., Makarov A., Mulyukova A., Baevd D., Khusnutdinova E., Tolstikova T., Dzhemilev U.
Current Cancer Drug Targets,
2015
10.
Carballeira N.M., Betancourt J.E., Orellano E.A., González F.A.
Journal of Natural Products,
2002
11.
Carballeira N.M., Montano N., Amador L.A., Rodríguez A.D., Golovko M.Y., Golovko S.A., Reguera R.M., Álvarez-Velilla R., Balaña-Fouce R.
Lipids,
2015
12.
Nemoto T., Yoshino G., Ojika M., Sakagami Y.
Tetrahedron,
1997
13.
Chen S., Hsu C., Li C., Lu J., Chuang L.
Food Chemistry,
2011
14.
Xie K., Miles E.A., Calder P.C.
Journal of Functional Foods,
2016
15.
D'yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.K., Khusnutdinova E.K., Dzhemilev U.M.
Chemical Communications,
2013
16.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Bioorganic and Medicinal Chemistry Letters,
2015
17.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Medicinal Chemistry Research,
2015
18.
D’yakonov V.A., Dzhemileva L.U., Tuktarova R.A., Makarov A.A., Islamov I.I., Mulyukova A.R., Dzhemilev U.M.
Steroids,
2015
19.
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Tuktarova R.A., Islamov I.I., Dzhemilev U.M.
Russian Chemical Bulletin,
2015
20.
Anderson L.C., Pinnick H.W.
Journal of Organic Chemistry,
1978
21.
D'yakonov V.A., Makarov A.A., Makarova E.K., Dzhemilev U.M.
Tetrahedron,
2013
22.
Coxon G.D., Douglas J.D., Minnikin D.E.
Chemistry and Physics of Lipids,
2003
23.
10.1016/j.mencom.2017.05.005_bib0115
Levy
Carbon-13 Nuclear Magnetic Resonance for Organic Chemists,
1972