CC(C[AlH]CC(C)C)C.[N:10]1([C:15]2[N:20]=[CH:19][C:18]([CH:21]=[CH:22][CH:23]=[O:24])=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[N:11]1.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.ClCCl.C(OCC)(=O)C>[N:10]1([C:15]2[N:20]=[CH:19][C:18]([CH:21]=[CH:22][CH2:23][OH:24])=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[N:11]1
DIBAL (1.0 M solution in toluene, 3.10 mL, 3.10 mmol) was added dropwise to a suspension of the compound from step B (350 mg, 1.53 mmol) in toluene (10 mL) and dichloromethane (4 mL) at −78° C. and the mixture was stirred for 2 h at that temperature. MeOH (1 mL) was added and the mixture was poured into a stirring mixture of ethyl acetate (20 mL) and 10% aq. potassium sodium tartrate (20 mL) and stirred for 1 h at RT. The organic layer was washed with brine (20 mL), dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded 185 mg (59%) of the title compound. MS 202 (M+H)+.
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