METHOD OF PRODUCING 11-CIS-RETINAL ISOMER Russian patent published in 2011 - IPC C07C403/14 C07C47/225 C07C45/62 

FIELD: chemistry.

SUBSTANCE: method involves Wittig olefination of the 6E-isomer of 2E-2,6-dimethyl-8-triphenylsilyloxyocta-2,6-dien-4-yn-1-al (synthon C₁₀)ylid, generated in situ from β-cyclogeranyltriphenyl phosphonium halide, removal of triphenylsilyl protection in the obtained silylated 13E-isomer of 11,12-didehydroretinol. After removal triphenylsilyl protection, the obtained 13E-isomer of 11,12-didehydroretinol is oxidised to 11,12-didehydroaldehyde using MnO₂ without extracting the semi-product separately and further purification procedures, and stereo-specific reduction of the triple bond in 11,12-didehydroaldehyde is then carried out in via hydrogenation on a Lindlar catalyst to obtain the desired 11-cis-retinal isomer, where generation of ylide from β-cyclogeranyltriphenyl phosphonium halide is carried out under the following conditions: a) NaH in tetrahydrofuran at 0-5°C, b) anhydrous K₂CO₃ in dichloromethane, in the presence of interphase transfer catalysts - quaternary ammonium salts at 20-25°C, or c) 1,2-epoxybutane in dichloromethane at 50-60°C.

EFFECT: obtaining medicinal agents for preventing or therapy of severe pathologies of the human optical system.

2 cl, 1 dwg, 1 tbl, 5 ex