Chemistry Letters p. 593 - 596 (1981)
Update date:2022-08-04
Topics:
Miyashita, Masaaki
Kumazawa, Toshiaki
Yoshikoshi, Akira
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 1-methoxy-2-methyl-1-<(trimethylsilyl)oxy>-1,3-butadiene and 2-nitropropene, while key intermediate 3,6-dimethyl-6-vinyl-6,7-dihydrobenzofuran-4(5H)-one was assembled by KF-catalyzed reaction of 5-methyl-5-vinyl-cyclohexane-1,3-dione and 1-nitro-1-phenylthiopropene.
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Doi:10.1002/ardp.19813140514
(1981)Doi:10.1039/c39810000581
(1981)Doi:10.1248/cpb.29.2078
(1981)Doi:10.1039/P19810002368
(1981)Doi:10.1016/S0040-4039(01)90545-3
(1981)Doi:10.1016/S0008-6215(00)80764-8
(1981)
