Synthesis of New Furan Derivatives and 4-Hydroxy Aldehydes from 4-Hydroxy 1-Enol Ethers

Alexandra Hölemann; Hans-Ulrich Reissig

doi:10.1055/s-2004-829175

PAPER

Synthesis of New Furan Derivatives and 4-Hydroxy Aldehydes from 4-Hydroxy 1-Enol Ethers

Alexandra Hölemann, Hans-Ulrich Reissig*
Institut für Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
Fax: +49(30)83855367; e-Mail: hans.reissig@chemie.fu-berlin.de;

Abstract

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Abstract

Starting from 4-hydroxy 1-enol ethers 3 different γ-lactols 4 were successfully prepared by acidic hydrolysis. Subsequent oxidation of 4 with pyridinium chlorochromate (PCC) led to γ-lactones 6 in good to excellent overall yields. Treatment of γ-lactols 4 with silylated nucleophiles 7 in the presence of Lewis acids afforded substituted tetrahydrofuran derivatives 8 in good to excellent yields. Additionally, different functionalized aldehydes 12, 13, and 14 were prepared employing the TBS-protected enol ether 11 as precursor. All these transformations demonstrate the synthetic versatility of compounds 3.

Key words

enol ethers - γ-lactols - γ-lactones - tetrahydrofuran derivatives - aldehydes

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