Sophorophenolone → Lupinalbin A

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 10 (0.17 g) and 7g Pyr-HCl was heated to 190° C. for 45 min. The reaction was allowed to cool and then partitioned between water and EtOAc. The EtOAc was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (EtOAc/hexanes; 3:7) to give the product as a white solid (0.07 g): Mp 318-322 (dec); 1H NMR (DMSO-d6) δ 12.90 (s, 1H), 10.97 (br s, 1H), 9.99 (br s, 1H), 7.72 (d, 1H, J=8.4 Hz), 7.11 (d, 1H, J=2.1 Hz), 6.93 (dd, 1H, J=8.4 Hz, 2.1 Hz), 6.56 (d, 1H, J=2.1 Hz), 6.30 (d, 1H, J=2.1 Hz); MS FI (neg) 283 (M−H)−.

Provenance & Evidence