Issue 22, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Hisahiro Hagiwara,*a   Kouji Sato,a   Daisuke Nishino,b   Takashi Hoshi,b   Toshio Suzukib  and  Masayoshi Andob  

* Corresponding authors

a Graduate School of Science and Technology, Niigata University, 8050, 2-nocho, Ikarashi, Niigata 950-2181, Japan

b Faculty of Engineering, Niigata University, 8050, 2-nocho, Ikarashi, Niigata 950-2181, Japan

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.

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

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Article information

DOI
https://doi.org/10.1039/B107180G
Article type
Paper
Submitted
07 Aug 2001
Accepted
26 Sep 2001
First published
02 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2946-2957

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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, T. Suzuki and M. Ando, J. Chem. Soc., Perkin Trans. 1, 2001, 2946 DOI: 10.1039/B107180G

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