METHOD OF STEREOSELECTIVE SYNTHESIS OF HETEROBICYCLIC ALCOHOL ENANTIOMER, INTERMEDIATE COMPOUNDS AND METHODS OF THEIR SYNTHESIS

摘要

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to a method of stereoselective synthesis of enantiomer of heterobicyclic alcohol. Invention concerns a method of synthesis of a pure enantiomer of the general formula (I): where X is O, S, NH or N-(C₁-C₄)-alkyl; Y₁ and Y₂ independently each of other means hydrogen atom or substituents taken among the group including halogen atom, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-group, (C₁-C₄)-haloidalkyl-group, formyl-group, nitro-group and cyano-group; atom C^* is in configuration R or S by reaction of compound of the general formula (II): where X, Y₁ and Y₂ have the same values given above; R₁ is hydrogen group or acceptable protecting group; R₂ is hydrogen atom; or R₁ and R₂ form in common optional mono- or di-(C₁-C₃)-alkyl-substituted methylene bridge with compound of the formula (III): where Z is hydroxyl or acceptable splitting off group; R₃ is a hydroxyl-protecting group; R₄ is halogen atom; or where R₃ and R₄ form in common valence bond or biradical of the formula -C(R₁₁)₂-O where R₁₁ is direct or branched (C₁-C₄)-alkyl-group; atom is in configuration R or S. As result of reaction compound of the general formula (IV): is formed where X, Y₁, Y₂, Y₃ and R₄ are given above; R₁ is hydrogen atom or protecting group followed by removal of protecting group by reaction of ring closing of the compound synthesized and by optional removal of protecting group from hydroxyl-group of product with closed ring. Invention relates also to enantiometrically pure intermediate compounds, methods of their synthesis and synthesis of the parent compound. Invention provides the development of economical method of synthesis of enantiomeric alcohol as an intermediate compound used in synthesis of biologically active compounds, for example, flesinoxane. EFFECT: improved methods of synthesis. 12 cl, 1 tbl