[O:1]=[C:2]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C1CCCCC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C1(C)C=CC=CC=1>[O:1]=[C:2]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]A mixture of 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (3.0 g) obtained in Example 13, a Lindlar catalyst (5% Pd-CaCO3 -PbO) (30 mg), cyclohexene (5.26 g) and toluene (12 ml) is charged in an atmospheric hydrogenation apparatus and subjected to reduction at room temperature under atmospheric pressure. After completion of the reaction, the catalyst is removed by filtration and the filtrate is concentrated to give 1-oxo-1-furyl-7-methoxycarbony-cis-4-heptene [VII-2] (2.74 g, yield; 90.4%).
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