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Compound 1 is the first alkaloid\u2013quassinoid adduct featuring a novel 6\/5\/5\/6\/6\/6-fused hexacyclic skeleton. Compounds 2 and 3 are unprecedented skeleton C19 quassinoids. Biosynthetic pathways were proposed, which guided the successful biomimetic synthesis of compound 1, affording an optimized yield of 23.2%. 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