The synthesis of topsentin‐A, a bisindole alkaloid isolated from the maring sponge Topsentia genitrix, has been achieved starting from 3‐acetylindole. Copyright © 1987 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim

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Synthesis of Topsentin‐A, A Bisindole Alkaloid of the Marine Sponge Topsentia genitrix

The reaction of 1,1-dimethyl-1-phenacylhydrazinium bromide with 1 M aqueous sodium hydroxide give benzoic acid, 3-phenyl-1-methylpyrazole, 5-benzoyl-3-phenyl-1-methylpyrazole, and benzonitrile as the major components; the expected product, 2-benzoyl-5-phenylimidazole was formed in only small amounts. Mechanisms to rationalize the formation of the major products are discussed.

The reaction of 1,1-dimethyl-1-phenacylhydrazinium bromide with aqueous sodium hydroxide.

X-ray crystal structure of 1,1-dimethyl-1-phenacylhydrazinium bromide. Evidence for intramolecular hydrogen bonding

The rearrangement of 1,1-dimethyl-1-phenacylhydrazinium bromide

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The rearrangement of 1,1-dimethyl-1-phenacylhydrazinium bromide

The rearrangement of 1,1-dimethyl-1-phenacylhydrazinium bromide