14402-57-4Relevant academic research and scientific papers
Synthesis of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents
Che, Zhi-Ping,Yang, Jin-Ming,Zhang, Song,Sun, Di,Tian, Yue-E,Liu, Sheng-Ming,Lin, Xiao-Min,Jiang, Jia,Chen, Gen-Qiang
, p. 163 - 175 (2020/03/03)
Endeavor to discover biorational natural products-based insecticides, two series (27) of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine were prepared and assessed for their insecticidal activity against Mythimna separata in?vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially derivatives 6l and 6o exhibited the best insecticidal activity with final mortality rates of 75.0% and 71.4%, respectively. Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9-substitution is well tolerated; the configuration of C8/9 position is important for insecticidal activity, and 9S-configuration is optimal; 6’-OCH3 moiety is not necessary, removal of it is also acceptable. (Figure presented.).
The First and Second Cinchona Rearrangement. Two Fundamental Transformations of Alkaloid Chemistry
Franz, M. Heiko,Roeper, Stefanie,Wartchow, Rudolf,Hoffmann
, p. 2983 - 2991 (2007/10/03)
Stereochemistry, products, and driving forces of the "first and second Cinchona rearrangement" have been investigated and a unified theory is presented. The first cage expansion affords [3.2.2]azabicyclic α-amino ether and is formulated via a configurationally stable bridgehead iminium ion and quasiequatorial nucleophilic attack. The second cage expansion affords β-functionalized [3.2.2]azabicycles. In this case a nonclassical nitrogen-bridged cation is postulated to account for retention of configuration and potential reversibility of the cage expansion. The second rearrangement is favored for the so-called cinch bases (6′-R = H) in trifluoroethanol. Stereoelectronic factors, electron demand at C9, ground state conformation, and solvent type are crucial in all cases. A two-step protocol for preparing 9-epi-configured Cinchona alkaloids from 9-nat precursors is described.
Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes Functionalized at carbon C3, from cinchonine and cinchonidine. Stereoselective solvolysis and an easily enolizable ketone
Roeper, Stefanie,Franz, M. Heiko,Wartchow, Rudolf,Hoffmann, H. Martin R.
, p. 4944 - 4946 (2007/10/03)
Solvolysis of C9 mesylated cinchonidine 1-OMs and cinchonine 2-OMs in solvent MeOH, EtOH, and CF3CH2OH affords ring-expanded 1-azabicyclo[3.2.2]nonanes oxygenated at carbon C3 ("second Cinchona rearrangement"). The newly introduced s
