METHOD FOR SYNTHESIS OF (+)- AND (-)-3-OXABICYCLO[3,3,0]OCT-6-EN-2-ONES Russian patent published in 2010 - IPC C07D307/88 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, specifically to a method for synthesis of (-)- and (+)-3-oxabicyclo[3.3.0]oct-6-en-2-ones with formulae

(I) and (II), involving reacting racemic 7,7-dichlorobicyclo[3.2.0]-hept-2-en-6-one with (+)-α-methylbenzylamine with formation of a mixture of diastereomeric amides, hydration of which leads to hydrolysis products - bicyclic aminals which are separated through column chromatography on SiO₂. Subsequent borohydride reduction of separate compounds leads to corresponding amido alcohols, acid hydrolysis of which leads to formation of enantiomerically pure target compounds - lactones (I) and (II) with total output of over 72% with respect to the initial compound.

EFFECT: simultaneous production of lactones I and II with high total output in enantiomerically pure form.

2 cl, 5 ex