[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[NH2:11])=[O:5])[CH3:2].[H-].[Na+].[CH3:14][C:15]([CH3:25])=[CH:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[BH4-].[Na+]>CN(C=O)C.CCOC(C)=O.CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]2[C:15]([CH3:25])([CH3:14])[CH2:16][CH:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:11][C:7]=12)=[O:5])[CH3:2]
Compound 1 (0.68 g, 4.41 mmol) was dissolved in DMF (5 mL). NaH (60% in mineral oil, 0.19 g, 4.7 mmol) was added at room temperature affording rapid gas evolution. The reaction stirred for 0.5 h upon which 3-methyl-1-phenyl-but-2-en-1-one (0.50 g, 3.15 mmol) was added. The reaction stirred for 0.5 h upon which EtOH (5 mL) and NaBH4 (1.19 g) were added. The solution was brought to 60° C. for 0.5 h. and then cooled to room temperature. The solution was quenched with water, extracted with Et2O (3 times), dried (Na2SO4) and concentrated. Flash chromatography (10% AcOEt) to give the desired product as a tan solid (0.60 g, 63% yield). MS Calcd.: 298. Found 299 (M+H).
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