METHOD OF PRODUCING LIGNAN, HAVING ANALGESIC ACTION Russian patent published in 2019 - IPC C07C69/753 C07C67/56 C07C67/297 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, mainly associated with synthesis of biologically active natural compounds – lignans and their synthetic analogues. A specific end product is a sevanol molecule which is a promising therapeutic agent for pain relief having the general formula given below. Disclosed method of chemical synthesis consists of 9 stages of synthesis, among which there are two principal chemical reactions: obtaining tri-tert-butyl ester of isocitric acid, by direct alkylation of di-tert-butyl ester of (L)-malic acid with tert-butyl bromoacetate using lithium diisopropylamide as a base at -78 °C in tetrahydrofuran and oxidative dimerisation of the corresponding caffeic acid derivative using a double excess of iron (III) chloride in a mixture of acetonitrile-water solvents in ratio of 4:1, respectively, at temperature 5 °C. In absence of light for 1 hour, which provides output of end product after stage of final chromatographic cleaning at level of 2.2 %. Besides, proposed method of producing leads to preferential formation of complete analogue of sevanol over isosevanol 75 % to 25 % respectively. Complete analog of sevanol in experiments in vivo is as good as biological activity of natural molecule isolated from natural raw material.

EFFECT: developed synthesis method can be used for creation of modified analogues of sevanol, for obtaining new biologically active lignans.

1 cl, 13 ex, 7 dwg