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Proposed mechanism for PhnB catalyzed conversion of 5 to 9. PhnB catalyzes the C2-hydroxlation of 5 through deprotonation of the hemiketal C13 hydroxyl group to yield 14. Deprotonation of C3-OH leads to rapid cyclization to form 16 which can undergo dehydration and aromatization to yield the product 9. Products that are not observed in the reaction, as well as substrate variants that do not react with PhnB are indicated.
