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Evolution of biosynthetic hypotheses regarding the origins of the hapalindoles and ambiguines: A. Moore's classic halonium (or proton) induced cyclization of β-ocimene (2). B. Carmeli's alternative one-step enzymatic cyclization to the tetracyclic hapalindole core (4). C. Liu's recent biosynthetic studies. D. Tetracyclic hapalindoles (4) and ambiguines (5) of interest in this synthesis campaign. GPP = geranyl pyrophosphate; DMAPP = dimethylallyl pyrophosphate; NHI = non-heme iron.
