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Synthesis of 3,10-dibromofascaplysin (8) and 3,8-dibromofascaplysin (9). Reagents and conditions: (a) 4-bromobutanal (25, 4.0 equiv.), EtOH, H2O, autoclave, 150 °C, 1 h; (b) 2,4-dibromoacetophenone (21a) (1 equiv.), I2 (0.8 equiv.), DMSO, 110 °C, 1 h, then tryptamines 26, 27 (1.0 equiv.), DMSO, 110 °C, 4 h; (c) 220 °C, 15 min, then HCl (aq).
