[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[C:31]([CH3:35])([CH3:34])[C:32]#[CH:33]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]2[O:21][C:31]([CH3:35])([CH3:34])[CH:32]=[CH:33][C:5]2=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[C:11]3[CH:17]=[CH:18][CH:19]=[CH:20][C:10]3=[CH:9][C:8]=1[NH:7]2To a solution of 2 g of the product of Step A in 50 ml of anhydrous dimethylformamide, under an inert atmosphere, there are added 2 g of anhydrous potassium carbonate. After stirring for 15 minutes at 65° C., 2.4 g of anhydrous potassium iodide and 4.4 g of 3-chloro-3-methyl-1-butyne are added, and the reaction mixture is held at 65° C. for 24 hours and then at 130° C. for 1 hour. After cooling, the solution is hydrolysed and then extracted with dichloromethane. The combined organic phases are washed with water and then with 1M potassium hydroxide solution, dried over sodium sulphate and then evaporated. After chromatography over silica gel (cyclohexane/acetone: 90/10), 1.10 g of the expected product are isolated.
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