Marine sponges produce a trio of compounds—sceptrin, massadine, and ageliferin—that have intrigued chemists because they seemed to result from ring-forming reactions outside the standard repertoire of enzyme catalysis. Ma et al. now report laboratory syntheses of the first two compounds that uncover a surprising twist: It turns out the real structure of sceptrin is the mirror image of the originally reported structure. The work partially bolsters the prevailing biosynthetic hypothesis, though its revelation of enantiodivergence (the emergence of distinct mirror-image motifs in one compound class) is a rare event in natural product chemistry.
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