An administration study of 2H-labeled precursors showed that the 9-hydroxydecanoyl unit, the acyl intermediate of lasiodiplodin (1), was also the intermediate of (5S)-5-hydroxylasiodiplodin (2) in Lasiodiplodia theobromae. The incorporation of [O-methyl-2H3]-lasiodiplodin (6) into 2 indicated that hydroxylation at C-5 occurred after cyclization.
