SYNTHESIS OF THE NATURAL ENANTIOMERS OF ASCOCHLORIN, ASCOFURANONE AND ASCOFURANOL

Article abstract of DOI:10.1016/S0040-4020(01)96657-8

Three fungal metabolites with a common structural feature as prenylated phenols were synthesized in their naturally occuring and optically active forms: ascochlorin <(2'E,4'E,1''R,2''R,6''R)-(-)-5-chloro-2,4-dihydroxy-6-methyl-3-<5'-(1'',2'',6''-trimethyl-3''-oxo-cyclohexyl)-3'-methyl-2',4'-pentadienyl>benzaldehyde>, ascofuranone <(2'E,6'E,1''S)-(-)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(3'',3''-dimethyl-4''-oxo-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl)benzaldehyde> and ascofuranol <2'E,6'E,1''S,4''S)-(-)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(3'',3''-dimethyl-4''-hydroxy-2''-oxacyclopentyl)-3',7'-dimethyl-2',6',-heptadienyl>benzaldehyde>. (+)-Ascofuranone and (+)-ascofuranol were also synthesized.By the present synthesis the absolute configuration of the natural (-)-ascofuranol was established as (1''S,4''S).