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Microbial transformation studies on 2β-angeloyloxy-5β,8β-dihydroxypresilphiperfolane have revealed that it was metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Mucor ramannianus (ATCC 9628) produced three metabolites. One of them was characterized as the novel metabolite (2'R,3'R)-(+)-2β-(2',3'-epoxyangeloyloxy)-5β,8β-dihydroxypresilphiperfolane on the basis of spectral data. The absolute configuration at both oxirane carbons was confirmed by hydrolysis product of the novel metabolite which is (2R,3R)-(+)-2,3-epoxyangelic acid.

Microbial Epoxidation of the Tricyclic Sesquiterpene Presilphiperfolane Angelate Ester