期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 71, 页码 17190-17194出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202003758
关键词
cymoside; furoindoline; monoterperne indole alkaloids; oxidative cyclisation; total synthesis
资金
- China Scholarship Council (CSC)
- ANR [ANR-15-CE29-0001]
- Universite Paris-Saclay
- CNRS
- Agence Nationale de la Recherche (ANR) [ANR-15-CE29-0001] Funding Source: Agence Nationale de la Recherche (ANR)
The second-generation synthesis of (-)-cymoside as well as the formation of a new hexacyclic-fused furo[3,2-b]indoline framework is reported. After a Pictet-Spengler condensation between secologanin tetraacetate and tryptamine, the course of the cyclization of the 7-hydroxyindolenine intermediate, generated by oxidation with an oxaziridine, depended on the stereochemistry of the 3-position. The 3-(S)-strictosidine stereochemistry delivered efficiently the scaffold of cymoside via intramolecular coupling with the C16-C17 enol ether, while the 3-(R)-vincoside stereochemistry directed towards the reaction with the C18-C19 terminal alkene and the formation of the unexpected caged compound.
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