Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols. Issue 46 (8th December 2022)

• Record Type: Journal Article
• Authors: Milyutin, Constantine V.; Galimova, Renata G.; Komogortsev, Andrey N.; Lichitsky, Boris V.; Migulin, Vasily A.; Melekhina, Valeriya G.
• Is Part Of: ChemistrySelect. Volume 7:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-08
• Subjects: allomaltol -- ESIPT-process -- oxygen heterocycles -- photochemistry -- tetrahydro-6H-cyclopenta[b]furan-6-ones; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202204000
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A novel UV‐mediated approach for the synthesis of previously unknown 3a, 6a‐dihydroxy‐4‐methyl‐2, 3, 3a, 6a‐tetrahydro‐6 H ‐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. Abstract : A novel photochemical method for the synthesis of substituted 3a, 6a‐dihydroxy‐4‐methyl‐2, 3, 3a, 6a‐tetrahydro‐6 H ‐cyclopenta[ b ]furan‐6‐ones from readily available allomaltols containing a 2‐aryl‐2‐hydroxyethyl fragment is described. For the first time, a side chain hydroxyl group was utilized for the final cyclization with photogenerated α‐hydroxy‐1, 2‐diketone fragment.