Methanol → Broussonin A

Participants

Reaction Steps

Yellow powder; mp 95-96° C.; UV (MeOH) λmax (log ε) 279 (3.67), 231 (3.82) nm; IR (NaCl) γmax 3380, 1625, 1558, 1507 cm 1; 1H NMR (CD3OD, 500 MHz) δ 1.78 (2H, m, H-2), 2.51 (4H, m, H-1 and H-3), 3.71 (3H, s, OCH3), 6.31 (1H, dd, J=2.5 and 8.1 Hz, H-5′), 6.33 (1H, d, J=2.4 Hz, H-3′), 6.67 (2H, d, J=8.6 Hz, H-3″), 6.90 (1H, d, J=8.2 Hz, H-6′), 6.98 (2H, d, J=8.5 Hz, H-2″); 13C NMR (CD3OD, 125 MHz) δ 30.3 (C-1), 33.5 (C-2), 35.9 (C-3), 55.6 (OCH3), 102.3 (C-3′), 105.4 (C-5′), 116.0 (C-3″), 122.5 (C-1′), 130.3 (C-2″), 131.4 (C-6′), 134.9 (C-1″), 156.2 (C-4″), 157.0 (C-2′), 160.3 (C-4′); EIMS m/z 258 (M+, 62), 151 (21), 137 (100), 107 (26).

Provenance & Evidence