<jats:title>Abstract</jats:title><jats:p>Seven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus <jats:italic>Aspergillus taichungensis</jats:italic> (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides C and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an <jats:italic>anti</jats:italic>‐bicyclo[2.2.2]diazaoctane core, whereas <jats:italic>A. protuberus</jats:italic> and <jats:italic>A. amoenus</jats:italic> produced congeners with a <jats:italic>syn</jats:italic>‐bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction.