[H][H].[BH4-].[Na+].C(N)CN.[OH:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[C:18][CH2:19][C:20]([OH:22])=[O:21].Cl>C(O)C.[OH-].[Na+].[Cl-].[Na+].O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[OH:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21]To a vigorously stirred mixture of nickel acetate (1 g) and absolute ethanol (25 mL), saturated with hydrogen, was added 5 mL of the filtrate from a solution of sodium borohydride (500 mg) in ethanol (12 mL) and 2N aqueous sodium hydroxide (0.63 mL). After hydrogen evolution had ceased, the black suspension was treated with 0.7 mL of ethylene diamine.6Alkyne 24 (643 mg, 3.0 mmol) was added and the reaction stirred for 1 hr at 23° C. The reaction was diluted with brine (100 mL), acidified with 5% HCl and extracted with ether (4×50 mL). The ether extract was washed with brine (2×50 mL). Product isolation gave 620 mg of 26 (96% yield).
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