Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition
Guillaume Bélanger, Clémence Hauduc
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00345

DOI: 10.1021/acs.joc.7b00345

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