title: Unusual reactions of a 7,17-seco-type C19-diterpenoid alkaloid derived from deltaline.
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.
authors: Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, Sichuan, PR China 610041.
authors: Ling
authors: L
authors: Wang
authors: Qiao-Hong
authors: QH
authors: Chen
authors: Feng-Peng
authors: FP
authors: Wang
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D004224:Diterpenes; C528313:deltaline