title: Alstoscholarisines H-J, Indole Alkaloids from Alstonia scholaris: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H.
abstract: Alstoscholarisines H-J (1-3), new monoterpenoid indole alkaloids with an unprecedented skeleton created via the formation of a C-3/N-1 bond, were isolated from Alstonia scholaris. Their structures were established by extensive spectroscopic analyses and the assessment of single-crystal X-ray diffraction data. The total synthesis of alstoscholarisine H was achieved via the regioselective nucleophilic addition of pyridinium through a bioinspired iminium ion intermediate followed by Pictet-Spengler-like cyclization.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Pan
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Xu-Jie
authors.initials: XJ
authors.lastname: Qin
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Ya-Ping
authors.initials: YP
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.|University of Chinese Academy of Sciences , Beijing 100049, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Xiao-Dong
authors.initials: XD
authors.lastname: Luo
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
mesh_terms: D031051:Alstonia / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D046948:Secologanin Tryptamine Alkaloids; C000608896:alstoscholarisine H