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.