6-Bromo-Nb-methoxycarbonyltryptamine (7) was prepared from 5-nitropyrroloindole (4a) by a series of reactions : reduction, bromination, deamination, and ring opening. Prenylation of 7 with an excess dimethylallyl bromide gave the 3a, 8-diprenylpyrroloindole (8). Hydrolysis of 8 followed by methylation with MeI-K2CO3-acetone provided (±)-flustramine B.
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Hino et al. (1983) studied this question.