The biotransformation of the phytoanticipin HBOA and its major degradation metabolites 2-hydroxy-N-(2-hydroxyphenyl)acetamide (7) and N-(2-hydroxyphenyl)acetamide (8) by Chaetosphaeria sp., an endophytic fungus isolated from Aphelandra tetragona, was studied. Three new metabolites could be identified as 2-amino-7-hydroxy-3H-phenoxazin-3-one (12), 2-acetylamino-7-hydroxy-3H-phenoxazin-3-one (13)...

Five new podocarpane-type trinorditerpenes were isolated from the bark of Taiwania cryptomerioides. Structures of 1beta, 14-dihydroxy-13-methoxy-6,8,11,13-podocarpatetraene (1), 1beta, 14-dihydroxy-13-methoxy-8,11,13-podocarpatriene (2), 13-hydroxy-12-methoxy-8,11,13-podocarpatrien-3-one (3), 14-hydroxy-13-methoxy-1,8,11,13-podocarpatetraen-3-one (4), and 13-methoxy-8,12-podocarpatriene-11,14-d...

A concise synthesis of (1S*,3R*,6R*)-1-hydroxy-7(14),10-bisaboladien-4-one, an antifeedant against the locust Locusta migratoria isolated from the Japanese cedar Cryptomeria japonica, was achieved by starting from 4-hydroxy-2-cyclohexenone.

A new compound, euparvic acid (1, C(14)H(16)O(6)), and the known compounds 5,7-dihydroxy-4-methylphthalide (2), 6-(3-carboxybutyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (3), 6-(5-carboxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (4), and 6-(5-carboxy-4-hydroxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (5) were isolated from the EtOAc extract of E...

Five new phenolic compounds, 4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl-propanone (8), 3-[5-[(threo) 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzofuranyl]-propanoic acid (12), 2-[4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenoxy]-3-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)propyl-beta-D-glucopyranoside (13), 4-[(erythro) 2,3-dihydro-3(hydroxymethyl)-5-(3-hydropropyl)...

The synthetic route for a uterine relaxant, bis(2-[[(2S)-2-([(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl]amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy]-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Brom...