Domino Michael–O-alkylation reaction: one-pot synthesis of 2, 4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

H Hagiwara, K Sato, D Nishino, T Hoshi…

Index: Hagiwara, Hisahiro; Sato, Kouji; Nishino, Daisuke; Hoshi, Takashi; Suzuki, Toshio; Ando, Masayoshi Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 22 p. 2946 - 2957

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Citation Number: 47

Abstract

The reaction of enolates of 1, 3-dicarbonyl compounds with α-halo-α, β-unsaturated carbonyl compounds affords 2, 4-diacyldihydrofuran derivatives in the presence of DBU in THF. Chemical manganese dioxide oxidation of the hydrofurans leads to 2, 4-diacylfuran derivatives. Application of the protocol enables short-step syntheses of antitumor naphthofuran natural products.