Two novel skeletal rearrangements involving in the C ring of C19-diterpenoid alkaloid deltaline derivatives.
Treatment of compounds 2 and 5, both from the C19-diterpenoid alkaloid deltaline 1, with 5% NaOH methanol (room temperature, 16 h) and NaOH-N,N-dimethylformamide (reflux, 10 h) led to the two novel skeletal rearrangement products 4 (90%) and 6 (62%), respectively, involving Wagner-Meerwein rearrangement and Grob fragmentation. Their structures were fully characteristized based on 2D NMR and HR-MS data.
Zou
Chun-Lan
CL
Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, No. 17, Duan 3 Renmin Nan Road, Chengdu 610041, PR China.
Liu
Xiao-Yu
XY
Wang
Feng-Peng
FP
Chen
Qiao-Hong
QH
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003640:Dealkylation; D031882:Delphinium / Q000737:chemistry; D004224:Diterpenes / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D004224:Diterpenes; D007202:Indicators and Reagents; C528313:deltaline