Synthetic racemate and enantiomers of cytosporone E, a metabolite of an endophytic fungus, show indistinguishably weak antimicrobial activity.
The racemate and the enantiomers of cytosporone E [3-heptyl-4,5,6-trihydroxyphthalide (1)], a metabolite of the endophytic fungus, CR200 (Cytospora sp.), were synthesized. The key steps were (i) Sharpless asymmetric dihydroxylation of an alkene (8) and (ii) HPLC separation of the enantiomers of tert-butyldimethylsilyl ether (12) on a chiral stationary phase. The racemate and enantiomers of cytosporone E showed only weak antimicrobial activity with no difference among them.
Ohzeki
Tomoya
T
Department of Chemistry, Graduate School of Science, Science University of Tokyo, Japan.
Mori
Kenji
K
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D005658:Fungi / Q000187:drug effects / Q000378:metabolism*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D001572:Benzofurans; C492581:cytosporone E