Inverted Prenylation of N_b-Methoxycarbonyltryptamine. Synthesis of 3a-(1, 1-Dimethylallyl) pyrrolo [2, 3-b] indole and 2-(1, 1-Dimethylallyl) tryptamine Derivatives

抄録

Reaction of the indolyl anion of N_b-methoxycarbonyltryptamine (4) with 2-chloro-2-methyl-3-butyne (2) gave the 3a-(1, 1-dimethylpropargyl) pyrrolo [2, 3-b] indole (6) along with the allene derivative (7) and N_a-(1, 1-dimethylpropargyl) tryptamine (8). Partial reduction of 6 gave the 3a-(1, 1-dimethylallyl) derivative (10), which rearranged to the 2-(1, 1-dimethylallyl) tryptamine (11) and the N_a-(3, 3'-dimethylallyl) tryptamine (12) on acid treatment. On the other hand, acid treatment of 6 gave the 2-(1, 1-dimethylpropargyl) tryptamine (14) in poor yield.