S(OC1CCC(C)=CC1)([C:4]1[CH:10]=C[C:7](C)=[CH:6][CH:5]=1)(=O)=O.Cl.O1[CH2:24][CH2:23][CH2:22][CH2:21]1>[Cl-].[Zn+2].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:21][C:22]1[CH2:7][CH2:6][CH:5]([C:4]#[CH:10])[CH2:24][CH:23]=1To a solution of lithium acetylide ethylenediamine complex (4.53 g) in dry tetrahydrofuran (38 mL), stirred and cooled to 0° C., is slowly added a 0.5M solution of zinc chloride in dry tetrahydrofuran (100 mL). The mixture is stirred at 10° C. for 30 minutes, then cooled to 0° C. again. A solution of tosylate 4D (R=methyl) (5 g) in dry tetrahydrofuran (11 mL) is then added dropwise, followed by addition of palladium tetrakis(triphenylphosphine) (650 mg). The reaction mixture is stirred overnight at room temperature. The mixture is poured into 10% HCl and extracted into ether. The combined organic layers are sequentially washed with a dilute sodium carbonate solution and brine, then dried over magnesium sulfate. The solvent is removed in vacuo.
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