(-)-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"/>
METHOD OF PRODUCING COREY LACTONE ENANTIOMERIC DERIVATIVES
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METHOD OF PRODUCING COREY LACTONE ENANTIOMERIC DERIVATIVES
METHOD OF PRODUCING COREY LACTONE ENANTIOMERIC DERIVATIVES
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机译：制备Corery内酯对映体衍生物的方法
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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
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机译：技术领域本发明涉及有机化学，尤其涉及一种制备式的科里内酯对映体衍生物的方法。 =“ 140” />（-）-Ia，b和（+）-Ia，b，其中涉及外消旋的5-羟基-4-（羟甲基）六氢-2H-环戊[b]呋喃-2-酮与三烷基-氯硅烷，然后将所得衍生物与（-）-（1R，4R，5S）-4-羟基-6,6-二甲基-3-氧杂双环[3.1.0]己-2-酮缩醛化，同时在无水沸腾在对甲苯磺酸催化剂的存在下苯形成非对映体酯，将其通过硅胶柱色谱分离，其中所述酯的甲醇解是通过在吡啶鎓盐对-甲基吡啶催化剂的存在下在甲醇中沸腾进行的。甲苯磺酸中1-1.25小时。所公开的方法使得能够获得对映体纯的所需化合物（（-）-Ia-c）和（（+）-Ia-c），相对于起始（±）-内酯二醇（II），其总产量为20-25％。 ）和对映体纯度≥97％.;效果：改进的方法; 5 cl，12 ex
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