BENZOMORPHAN ANALOGOUS CNS AGENTS - SYNTHESIS OF HOMOCHIRAL EPOXYBENZOCYCLOOCTENAMINES

The crucial steps in the preparation of the enantiomerically pure amin e 5 from the enol ester 3 are: 1. Stereoselective reduction of the eno l ester 3 to give the beta-hydroxy ester 6; 2. elimination of the hydr oxy group of 6 according to the method of Barton and McCombie; 3. Hofm ann rearrangement of the amid 12 with [bis(trifluoroacetoxy)iodo]benze ne to yield the ammonium chloride 14.HCl. In contrast to the racemic a mines (+/-)-1a and (+/-)-2a the homochiral amine 5 did not influence t he behaviour of mice. Therefore, we conclude that 5 after intraperiton eal application has no effects on the central nervous system.