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Unusual reactions of a 7,17-seco-type C19-diterpenoid alkaloid derived from deltaline
- Source :
- Natural product communications. 7(6)
- Publication Year :
- 2012
-
Abstract
- Treatment of a 7,17-seco-type C19-diterpenoid alkaloid (3), prepared from deltaline (8), with triethylamine in either DMF or TEG (triethylene glycol) at 120 degrees C provided two interesting compounds 6 and 7. The structures of compounds 3, 6, and 7 were established based on extensive interpretations of their 1D and 2D NMR data. Compound 6, a lycoctonine-type C19-diterpenoid alkaloid, can be transformed from alkaloid 3 via Grob fragmentation, Prins reaction, and intramolecular disproportionation. The mechanism of the formation of compound 6 was confirmed by deuteration experiments. Product 7 was formed through a pinacol-like rearrangement of alkaloid 3.
- Subjects :
- Alkaloids
Magnetic Resonance Spectroscopy
Molecular Structure
Diterpenes
Subjects
Details
- ISSN :
- 1934578X
- Volume :
- 7
- Issue :
- 6
- Database :
- OpenAIRE
- Journal :
- Natural product communications
- Accession number :
- edsair.pmid..........92ef339f8e6397490134dfaf1c7ca6fc