Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine

被引:11
|
作者
Yang, Lijuan [2 ,3 ]
Wang, Xuequan [1 ]
Pan, Zhiqiang [1 ]
Zhou, Ming [1 ]
Chen, Wen [2 ,3 ]
Yang, Xiaodong [1 ]
机构
[1] Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
[2] Yunnan Univ Nationalities, Key Lab Ethn Med Resource Chem, State Ethn Affairs Commiss, Kunming 650031, Yunnan, Peoples R China
[3] Minist Educ, Kunming 650031, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
Amaryllidaceae alkaloids; crinine; oxocrinine; total synthesis; quaternary carbon; AZA-COPE REARRANGEMENTS; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTION; SCELETIUM ALKALOIDS; ANTIMALARIAL ACTIVITY; LYCORINE;
D O I
10.1055/s-0030-1259288
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A flexible strategy leading to the synthesis of crinine-type Amaryllidaceae alkaloids, (+/-)-oxocrinine and (+/-)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.
引用
收藏
页码:207 / 210
页数:4
相关论文
共 21 条
  • [1] Crinine-type alkaloids from Hippeastrum aulicum and H-calyptratum
    Paulo de Andrade, Jean
    Guo, Ying
    Font-Bardia, Merce
    Calvet, Teresa
    Dutilh, Jullie
    Viladomat, Francesc
    Codina, Carles
    Nair, Jerald J.
    Silveira Zuanazzi, Jose A.
    Bastida, Jaume
    PHYTOCHEMISTRY, 2014, 103 : 188 - 195
  • [2] Development of an Intramolecular Aryne Ene Reaction and Application to the Formal Synthesis of (±)-Crinine
    Candito, David A.
    Dobrovolsky, Dennis
    Lautens, Mark
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (37) : 15572 - 15580
  • [3] Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization
    Du, Kang
    Yang, He
    Guo, Pan
    Feng, Liang
    Xu, Guangqing
    Zhou, Qinghai
    Chung, Lung Wa
    Tang, Wenjun
    CHEMICAL SCIENCE, 2017, 8 (09) : 6247 - 6256
  • [4] Synthesis of Amaryllidaceae alkaloids, siculine, oxocrinine, epicrinine, and buflavine
    Kodama, S
    Takita, H
    Kajimoto, T
    Nishide, K
    Node, M
    TETRAHEDRON, 2004, 60 (22) : 4901 - 4907
  • [5] Bioinspired Total Synthesis of Montanine-Type Amaryllidaceae Alkaloids
    Bao, Xu
    Cao, Ye-Xing
    Chu, Wen-Dao
    Qu, Hu
    Du, Ji-Yuan
    Zhao, Xian-He
    Ma, Xiao-Yan
    Wang, Cheng-Tao
    Fan, Chun-An
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14167 - 14172
  • [6] Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids
    Pandey, Ganesh
    Gupta, Nishant R.
    Gadre, Smita R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (04) : 740 - 750
  • [7] Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids
    Wang, Fang
    Xu, Xiaohan
    Yan, Yangtian
    Zhang, Jiayang
    Yang, Yang
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) : 668 - 672
  • [8] Synthesis of the tetracyclic skeleton of the galanthamine-type Amaryllidaceae alkaloids
    Herke, Klara
    Hazai, Laszlo
    Hudak, Mate Szabolcs
    Abraham, Janka
    Santa, Zsuzsanna
    Hada, Viktor
    Szantay, Csaba, Jr.
    Szantay, Csaba
    ARKIVOC, 2009, : 235 - 246
  • [9] The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly
    Hu, Nan
    White, Lorenzo V.
    Lan, Ping
    Banwell, Martin G.
    MOLECULES, 2021, 26 (03):
  • [10] Synthetic studies of hetisan-type aconite alkaloids -: Total synthesis of (±)-nominine
    Muratake, H
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2006, 64 (03) : 237 - 250