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A New and Facile Synthesis of Rutaecarpine Alkaloids. -An appropriate general construction strategy for the synthesis of rutaecarpine alkaloids is applied to furnish the rutaecarpine analogues (III). The concise procedure involves a unique one-pot reductive-cyclization reaction, cf. (II) -> (III), as the key step. Key intermediates (II) are prepared from tryptamine following acylation, Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond. Chlororutaecarpine (IIIc) displays an extraordinarily inhibitory effect on platelet aggregation induced by arachidonic acid.

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