Scheme 4.
Reinvestigation of the [2+2] photocycloaddition of ent-zingiberene (ent-3) and hyperolactone C (4). Synthesis of biyouyanagin A (1), B (2, revised structure) and C (16). Reagents and conditions: 4 (1.0 equiv), ent-3 (20.0 equiv), 2′-acetonaphthone (1.0 equiv), CH2Cl2, 320 nm, 5 °C, 12 h; 51 % yield (1); 3 % yield (2); 2 % yield (15).