Tetrahedron p. 3049 - 3062 (1985)
Update date:2022-08-03
Topics:
Mori, Kenji
Takechi, Shozo
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).
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Doi:10.1007/BF00955380
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