[CH3:1][C@@H:2](N(C)C)[C@@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:14][C:15](C)([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:16]#C.C1(C=O)CCCCC1>[O-]S(C(F)(F)F)(=O)=O.[Zn+2].[O-]S(C(F)(F)F)(=O)=O.C(N(CC)CC)C>[CH:4]1([C@@H:3]([OH:10])[C:2]#[C:1][C:15]([CH3:16])([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH3:14])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1A flask is charged with zinc triflate (545 mg, 3 mol % based on the aldehyde compound mentioned blow). Vacuum (0.5 hPa or lower) is applied and the flask is heated to 125° C. for 2 hours. The flask is cooled to 23° C., the vacuum released and (+)-N-methylephedrine (296 mg, 3.3 mol % based on the aldehyde compound mentioned below) is added. Vacuum (0.5 hpa or lower) is applied for 0.5 hour and then released. To the flask, triethylamine (607 mg, 12 mol % based on the aldehyde compound mentioned below) and 2-(1,1-dimethyl-prop-2-ynyloxy)-tetrahydropyran as the alkyne compound (55 mmol, 110 mol % based on the aldehyde compound mentioned below) are added, and stirred for 0.25 hour at 25-30° C. And then cyclohexanecarboxaldehyde (50 mmol) as the aldehyde compound is added. The reaction mixture is stirred at 50° C. for 20 hours. Then, the distillation under reduced pressure gives (R)-1-cyclohexyl-4-methyl-4-tetrahydropyranyloxy-2-pentyn-1-ol, bp 130° C. (0.04 hPa), a colorless oil, in 82% yield.
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