Process for preparing enantiomeric derivatives of Corey lactone

摘要

FIELD: chemistry.;SUBSTANCE: invention relates to organic chemistry, specifically to a method of producing Corey lactone enantiomeric derivatives of formulae (-)-Ia,b and (+)-Ia,b, which involves reacting racemic 5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one with trialkyl-chlorosilane, followed by acetalisation of the obtained derivatives with (-)-(1R,4R,5S)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one while boiling in anhydrous benzene in the presence of a para-toluene sulphonic acid catalyst to form diastereomeric esters which are separated by column chromatography on silica gel, wherein methanolysis of said esters is carried out by boiling in methanol in the presence of a catalyst of a pyridinium salt para-toluene sulphonic acid for 1-1.25 hours. The disclosed method enables to obtain enantiomerically pure desired compounds ((-)-Ia-c) and ((+)-Ia-c) with total output of 20-25% with respect to the starting (±)-lactone diol (II) and enantiomeric purity of ≥97%.;EFFECT: improved method.;5 cl, 12 ex