Masaaki Miyashita, Toshiaki Kumazawa, Akira Yoshikoshi
1981
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0
Influential Citations
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Journal
Chemistry Letters
Abstract
Curzerenone and epicurzerenone were synthesized by means of a combination of γ-ketoester synthesis and 3-methylfuran annulation both of which utilize nitroolefins as synthons. Starting material, methyl 2-methyl-4-oxo-2-vinylpentanoate, was prepared by the Lewis acid-promoted reaction of l-methoxy-2-methyl-l-[(trimethylsily)oxy]-1,3-butadiene and 2-nitropropene, while key intermediate 3,6-dimethyl-6-vinyl-6,7-dihydrobenzofuran-4(5H)-one was assembled by the KF-catalyzed reaction of 5-methyl-5-vinylcyclohexane-l,3-dione and 1-nitro-1-phenylthiopropene.