CHEMO-ENZYMATIC SYNTHESIS OF NAATURAL PRODUCTS: SYNTHESIS OF SPHYDROFURAN

Article abstract of DOI:10.1016/S0040-4039(00)92071-9

A novel synthesis for sphydrofuran 1 has been developed.Starting with achiral materials the chiral centers of the target molecule were introduced via enzymatic methods as well as via a diastereoselective Grignard reaction.Rabbit muscle aldolase (RAMA)-catalyzed aldol condensation of chloroacetaldehyde 3 with dihydroxyacetone phosphate (DHAP) 4 affords the C-5 skeleton of 5 which was transformed to sphydrofuran 1 and its analogue 10 via a Grignard addition of allylmagnesium bromide followed by a Wacker reaction.