title: Biomimetic conversion of aconitine-type C19-diterpenoid alkaloids to lactone-type alkaloids.
abstract: The first biomimetic conversion from the aconitine-type C(19)-diterpenoid alkaloids to the corresponding alkaloids of lactone-type C(19)-diterpenoid alkaloid has been achieved. Chasmanine was used as starting material with Baeyer-Villiger oxidation as a key reaction. It was also observed that the oxygenated group at C-16 did not change the relative migration tendencies of C-13 and C-9 during the oxidation. Meantime, a novel D-ring fragmented compound was obtained during the course of the present investigation. The plausible mechanism of the formation of this compound was also proposed.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, China.
authors.forename: Meng
authors.initials: M
authors.lastname: Zhu
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Liu
authors.forename: Qiao-Hong
authors.initials: QH
authors.lastname: Chen
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D000157:Aconitine / Q000138:chemical synthesis / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000470:Alkaloids; D004224:Diterpenes; D007783:Lactones; D000157:Aconitine