Journal
SYNLETT
Volume 24, Issue 15, Pages 1941-1944Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1339472
Keywords
strictamine; oxidative coupling; indole alkaloid; tetrahydro--carboline
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Funding
- EPFL
- Swiss National Science Foundation (SNSF)
- Swiss National Centers of Competence in Research (NCCR)
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A synthetic approach featuring a key intramolecular oxidative coupling of a dianion for the formation of the C7-C16 bond was exploited aiming at the synthesis of strictamine. Treatment of substituted tetrahydrocarboline with LHMDS at -78 degrees C followed by iodine at room temperature afforded a tetracyclic compound, a substructure of eburnane-type alkaloid, via the formation of the N-a-C16 bond.
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