Tetrahedron letters

A novel synthetic method of dihydro-4-pyrone derivatives and its application to the syntheses of ar-atlantone and (±)-ar-turmerone

T Sakai, K Miyata, M Ishikawa, A Takeda

Index: Sakai, Takashi; Miyata, Kazuyoshi; Ishikawa, Mutsumi; Takeda, Akira Tetrahedron Letters, 1985 , vol. 26, # 39 p. 4727 - 4730

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Citation Number: 20

Abstract

Abstract Reaction of 1, 3-dihalo-3-methy]-2-butanone with t-butyl acetoacetate (NaH) gave t- butyl 3, 4-dihydro-2, 2, 6-trimethyl-4-oxo-2H-pyran-5-carboxylate via the Favorskii-type rearrangement. Michael addition of 4-methylphenyllithium (CuI) followed by ring cleavage with Me 3 SiCl-NaI in DMF or PrCN afforded ar-atlantone as well as (±)-ar-turmerone selectively.