title: An O-to-N intramolecular acyl migration in C₁₉-diterpenoid alkaloids.
abstract: The O-acyl group at C-1 of two C₁₉-diterpenoid alkaloids 2 and 5 was transferred to the secondary amine nitrogen to form amides 3 and 6 in the basic condition. This kind of O-to-N intramolecular acyl migration could be caused by the near distance between the nucleophilic nitrogen atom and the carbonyl group of the ester at C-1 in the C₁₉-diterpenoid alkaloids, which is consistent with the conformation of rings A and E in the C₁₉-diterpenoid alkaloids.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Qi-Feng
authors.initials: QF
authors.lastname: Chen
authors.forename: Xi-Xian
authors.initials: XX
authors.lastname: Jian
authors.forename: Qiao-Hong
authors.initials: QH
authors.lastname: Chen
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D004224:Diterpenes / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000470:Alkaloids; D000588:Amines; D004224:Diterpenes