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The development of a new one-pot reaction sequence afforded the tricyclic core of several aspidospermatan-type alkaloids from a linear, densely functionalized substrate. The key sequence features a highly chemoselective formamide activation that triggered a Vilsmeier-Haack cyclization, followed by an azomethine ylide generation and intramolecular cycloaddition. The choice of nucleophile, azomethine ylide precursor, and dipolarophile was crucial to the success of the sequence.

General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition