Scheme 12. Attempted Hydrazone–Boronic Acid Coupling on Protected Ouabageninone 62.
Reagents and conditions: (a) TrisNHNH2 (1.5 equiv), CH2Cl2, 23 °C, 10 h, 80%; (b) 76 (2 equiv), K2CO3 (2.2 equiv), dioxane, 110 °C, 5 h; (c) TMSOTf (3 equiv), Et3N (4 equiv), 23 °C, 1 h; (d) Ac2O (3 equiv), pyridine (7 equiv), DMAP (1 equiv), DMF, 40 °C, 20 h, 66%; (e) MOMCl (2.4 equiv), iPr2EtN (3.5 equiv), DMAP (1 equiv), CH2Cl2, 0 to 23 °C, 24 h, 62%.