Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)-Myrioneurinol

被引：27
作者：
Nocket, Anthony J. [1 ]
Weinreb, Steven M. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 51期
基金：
美国国家科学基金会;
关键词：
alkaloids; Michael addition; natural products; nitrogen heterocycles; total synthesis; FUSED TRICYCLIC AMINES; MYRIONEURON-NUTANS; BIOMIMETIC SYNTHESIS; DIPOLAR CYCLOADDITION; NITRARIA ALKALOIDS; ACYCLIC ALDEHYDES; MICHAEL REACTION; (+)-ISONITRAMINE; MYRIOXAZINE; CYCLIZATION;
D O I：
10.1002/anie.201407810
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid (+/-)-myrioneurinol has been accomplished using three highly diastereoselective reactions as pivotal steps: 1) an intramolecular Michael addition of a benzyloxycarbonyl-protected lactam titanium enolate to an alpha,beta-unsaturated ester for construction of the spirocyclic C5 quaternary center and the a/d rings, 2) a malonate anion conjugate addition to a transient nitrosoalkene to install the requisite functionality and configuration at the C7 position, and 3) an intramolecular sulfonyliminium aza-Sakurai reaction to form the b ring and the attendant C9/C10 configuration of the natural product.
引用
收藏
页码：14162 / 14165
页数：4
相关论文
共 50 条
  • [21] Total synthesis of the cytotoxic alkaloid luotonin A
    Wang, HS
    Ganesan, A
    TETRAHEDRON LETTERS, 1998, 39 (49) : 9097 - 9098
  • [22] Total Synthesis of (+)-Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization
    Zhang, Ze-Xin
    Chen, Si-Cong
    Jiao, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (28) : 8090 - 8094
  • [23] Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis
    Smith, Joel M.
    Moreno, Jesus
    Boal, Ben W.
    Garg, Neil K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 400 - 412
  • [24] Concise Total Synthesis of the Frog Alkaloid (-)-205B
    Tsukanov, Sergey V.
    Comins, Daniel L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8626 - 8628
  • [25] Total Synthesis of the Indole Alkaloid (±)- and (+)-Methyl N-Decarbomethoxychanofruticosinate
    Wei, Yi
    Zhao, Duo
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12988 - 12991
  • [26] Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and ConidiogenoneB
    Hou, Si-Hua
    Tu, Yong-Qiang
    Wang, Shuang-Hu
    Xi, Chao-Chao
    Zhang, Fu-Min
    Wang, Shao-Hua
    Li, Yan-Tao
    Liu, Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4456 - 4460
  • [27] Synthesis of imbiline 1, a tetracyclic aza-aromatic alkaloid
    Kitahara, Y
    Mochii, M
    Mori, M
    Kubo, A
    TETRAHEDRON LETTERS, 2000, 41 (09) : 1481 - 1482
  • [28] Stereocontrolled total synthesis of the Stemona alkaloid (-)-stenine
    Morimoto, Y
    Iwahashi, M
    Kinoshita, T
    Nishida, K
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (19) : 4107 - 4116
  • [29] Total Synthesis of Indole Alkaloid Alsmaphorazine D
    Zhu, Chenlong
    Liu, Zhaobo
    Chen, Guanyu
    Zhang, Kai
    Ding, Hanfeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) : 879 - 882
  • [30] Efficient Total Synthesis of Marine Alkaloid (-)-Nakadomarin A
    Cheng, Bin
    Wu, Fufang
    Yang, Xiaobao
    Zhou, Yuedong
    Wan, Xiaolong
    Zhai, Hongbin
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) : 12569 - 12572
12345