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TOTAL SYNTHESIS OF CURZERENONE AND EPICURZERENONE
Miyashita, Masaaki,Kumazawa, Toshiaki,Yoshikoshi, Akira
, p. 593 - 596 (2007/10/02)
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--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.
