FIELD: organic chemistry, chemical technology, medicine.
SUBSTANCE: invention relates to a new method for synthesis of 4α-arylepicatechine, in particular, to a method for synthesis of epicatechin-4α,8-epicatechin dimer that involves the following steps: (a) protection of C-3 hydroxyl group on 5,7,3',4'-tetra-O-benzylepicatechin molecule with benzyl protecting group to form 3,5,7,3',4'-penta-O-benzylepicatechin; (b) oxidation of epicatechin at position 4 from step (a) to obtain 3,5,7,3',4'-penta-O-benzyl-4-hydroxyepicatechin; (c) oxidation of hydroxy-group at position C-4 in epicatechin molecule from step (b) to obtain (2R,3S)-3,5,7,3',4'-penta-O-benzyl-4-ketone epicatechin; (d) addition of tert.-butyl lithium to 3,5,7,3',4'-penta-O-benzyl-8-bromoepicatechin to obtain reagent of protected epicatechin lithium; (e) addition of epicatechin from step (c) to reagent of epicatechin lithium from step (d) to obtain 3,5,7,3',4'-penta-O-benzyl-4-hydroxyepicatechine-4α,8-(3,5,7,3',4'-penta-O-benzyl)-epicatechin dimer; (f) reduction of hydroxyl group at position C-4 in dimer molecule from step (e) to obtain 3,,5,7,3',4'-penta-O-benzylepicatechin-4α,8-(3,5,7,3',4'-penta-O-benzyl)-epicatechin dimer, and (g) substitution of benzyl groups in dimer from step (f) for hydrogen atoms to obtain epicatechin-4α,8-epicatechine dimer. Also, invention relates to alternative variant of a method for preparing epicatechin-4α,8-epicatechine dimer and to new intermediate substances. Invention provides the development of new stereoselective method for synthesis of epicatechine-4α,8-epicatechin dimer that relates to class of proanthocyanidins eliciting the inhibitory activity with respect to different cancer lines.
EFFECT: improved method of synthesis, valuable medicinal properties of compounds.
11 cl, 20 ex
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