Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 9, Pages 4703-4712Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00345
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Funding
- Natural Science and Engineering Research Council (NSERC) of Canada
- Universite de Sherbrooke
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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 cydlization, 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.
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