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Significance: Hydroxy fatty acids (HFAs) have a wide range of applications as fragrances, food supplements, and pharmaceuticals. The direct, regioand enantioselective C–H hydroxylation of nonactivated fatty acids would provide an elegant and efficient approach toward HFAs. Flitsch and co-workers report the first example of a regioand stereoselective C5 hydroxylation of decanoic acid (1) to give (S)-5-hydroxydecanoic acid (2), catalyzed by a wild-type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus). Acid-catalyzed cyclization of 2 gave access to the lactonization product (S)--decalactone (3), a high-value fragrance compound. Comment: Methodologies for the proximal and -positions or the terminal -1, -2 and -3-hydroxy acids have been investigated in the past. The mid-chain and -positions have previously been synthesized from functionalized materials. The authors explain the high enantioselectivity of the C–H oxyfunctionalization in terms of molecular docking of acid 1 with the active site of P450-TT. Accordingly, substrate 1 folds in a U-shaped conformation and is placed above the heme prosthetic group, permitting hydroxylation in the middle of the chain, giving access to the (S)-enantiomer at C5. It is noteworthy that further engineering of this protein family might enable utilization of a variety of nonactivated substrates.

Valorization of a Saturated Fatty Acid to Enantioenriched (S)-δ-Decalactone