1985•Chemical and Pharmaceutical BulletinOpen access

Inverted prenylation of Nb-methoxycarbonyltryptamine. Synthesis of 3a-(1,1-dimethylallyl)pyrrolo(2,3-b)indole and 2-(1,1-dimethylallyl)tryptamine derivatives.

Tohru Hino, Koichi Hasumi, HITOSHI YAMAGUCHI, Mikio Taniguchi, Masako Nakagawa

Abstract

Reaction of the indolyl anion of Nb-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 Na-(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 Na-(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.

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Key concepts: Tryptamine, Chemistry, Indole test, Stereochemistry, Allene, Derivative (finance), Yield (engineering), Pictet–Spengler reaction