[CH3:1][CH2:2]OCC.[CH2:6]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:7]1[O:9][CH2:8]1.C([Mg]Cl)=C.[Cl-].[NH4+]>C1COCC1.[Cu]I>[CH2:11]([O:10][CH2:6][C@H:7]([OH:9])[CH2:8][CH:1]=[CH2:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Ether (100 ml) and copper(I) iodide (580 mg) were added to a solution of (R)-benzyl glycidyl ether (10.0 g) in THF (100 ml). The mixture was cooled to −78° C., and vinylmagnesium chloride (1.38 M, 53.0 ml) was added dropwise. The mixture was stirred overnight with gradual heating to room temperature. Ice was added to the reaction solution, and an ammonium chloride solution was further added. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with an ammonium chloride solution. The insoluble matter was removed by filtration through celite, and the solvent was evaporated under reduced pressure to obtain the title compound (12.5 g).
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