Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2022, Volume: 7, Number: 46, Article number : e202204000, Pages count : DOI: 10.1002/slct.202204000

Authors

Milyutin Constantine V. ¹ , Galimova Renata G. ^2,1 , Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Migulin Vasily A. ¹ , Melekhina Valeriya G. ¹

Affiliations

1	Laboratory of Heterocyclic Compounds, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow, 119991 Russian Federation
2	Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory, 1, Moscow, 119991 Russian Federation

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.

Milyutin C.V. , Galimova R.G. , Komogortsev A.N. , Lichitsky B.V. , Migulin V.A. , Melekhina V.G.
Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols
ChemistrySelect. 2022. V.7. N46. e202204000 . DOI: 10.1002/slct.202204000 WOS Scopus OpenAlex

Web of science:	WOS:000894286300001
Scopus:	2-s2.0-85144229662
OpenAlex:	W4312106819

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