Chemistry Letters

TOTAL SYNTHESIS OF CURZERENONE AND EPICURZERENONE

M Miyashita, T Kumazawa, A Yoshikoshi

Index: Miyashita, Masaaki; Kumazawa, Toshiaki; Yoshikoshi, Akira Chemistry Letters, 1981 , p. 593 - 596

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Citation Number: 4

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 ...

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