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2005
Furan derivatives
R 0060
Synthesis of New Furan Derivatives and 4-Hydroxy Aldehydes from 4-Hydroxy
Ethers. — The utility of 4-hydroxy enol ethers (I) and (III) as building block
01- 092 1-Enol
in the synthesis of different furan derivatives is demonstrated. Thus, acid hydrolysis
and subsequent oxidation with PCC leads to γ-lactones (II) in good to excellent yield.
Acid hydrolysis of (III) followed by treatment with silylated nucleophiles like (VI) and
(VIII) in the presence of Lewis acids affords substituted tetrahydrofuran derivatives
(VII) and (IX), respectively. Additionally, different functionalized aldehydes (XIII),
(XIV) and (XV) are prepared employing the Tbs-protected enol ethers (XII) as precursor. — (HOELEMANN, A.; REISSIG*, H.-U.; Synthesis 2004, 12, 1963-1970; Inst.
Chem., FU Berlin, D-14195 Berlin, Germany; Eng.) — Bartels
2005
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