A novel UV‐mediated approach for the synthesis of previously unknown 3a,6a‐dihydroxy‐4‐methyl‐2,3,3a,6a‐tetrahydro‐6H‐cyclopenta[b]furan‐6‐one derivatives from easily accessible substituted allomaltols containing a 2‐aryl‐2‐hydroxyethyl fragment was elaborated. The suggested method is based on the ESIPT‐promoted contraction of a 3‐hydroxy‐4‐pyranone moiety followed by intramolecular trapping of a photogenerated α‐hydroxy‐1,2‐diketone intermediate. For the first time, we have demonstrated that a side chain hydroxyl group can be employed for the concluding cyclization with a labile α‐hydroxy‐1,2‐diketone fragment. The structure of one synthesized photoproduct was determined by X‐ray diffraction.
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