Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
Abstract
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. View Full-Text
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Ban, Y.; Ashida, Y.; Nakatsuji, H.; Tanabe, Y. Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition. Molbank 2016, 2016, M908.
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