ENZYMATIC KINETIC RESOLUTION OF Y-4-OXA-ENDO-TRICYCLO[5.2.1.0(2,6)]DEC-8-EN-3-ONES - A USEFUL APPROACH TO D-RING SYNTHONS FOR STRIGOL ANALOGS WITH REMARKABLE STEREOSELECTIVITY

Racemic xy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methy l analogue were resolved employing a lipase-catalyzed acetylation reac tion. The latter compound thus gave access to a homochiral D-ring synt hon for strigolactones. The enzymatic acetylation reaction occurred wi th a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acet oxy-2(5H)-furanone.