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Unusual reactions of a 7,17-seco-type C19-diterpenoid alkaloid derived from deltaline
Ling Wang1, Qiao-Hong Chen, Feng-Peng Wang
1Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, Sichuan, PR China 610041.
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.
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