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Lactones 18 : synthesis of bicyclic lactones with methyl-, di- and trimethyl substituted cyclohexane system.
Autorzy
Rok wydania
2005
Czasopismo
Numer woluminu
79
Strony
1763-1771
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Starting from racemic γ,δ-unsaturated esters (1a-d) twelve bicyclic γ-lactones with the cyclohexane system substituted with various number of methyl groups were synthesized. The esters mentioned were subjected to the alkaline hydrolysis and then to iodolactonization to furnish the corresponding iodolactones (3a-d). The reduction of these compounds with tributyltin hydride gave the saturated lactones (4a-d) whereas the dehydrohalogenation with DBU yielded their unsaturated analogues (5a-d). The structures of all lactones obtained were established by their spectral ( 1H NMR, IR) data. For two of them the crystal structures were determined.
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