Scheme 2.
(±)-Aurantioclavine. Reagents and conditions: (a) NEt3, MeOH (1:1), room temperature, 10 h; (b) Tf2O, NEt3, CH2Cl2, 0 °C, 0.5 h, 60% (2 steps); (c) 10% Pd/C, HCO2NH4 (4 equiv.), MeOH, room temperature, 0.5 h, 35% 2, 18% 39, 28% 44; (d) PdCl2(PPh3)2, dppp, NEt3, HCO2H, DMF, 100 °C, 2 h, 43%.