First Total Synthesis of a Cytotoxic Derivative of the Natural Product Aaptamine

被引:2
|
作者
Puvvala, Srinu [1 ,2 ]
Jadhav, Vinod D. [1 ]
Narkhede, Umesh C. [1 ]
Karun, M. V. V. S. R. N. Anji [1 ]
Reddy, Ch. Venkata Ramana [2 ]
机构
[1] GVK Biosci Pvt Ltd, Chem Serv, IDA Nacharam, Hyderabad 500076, Andhra Pradesh, India
[2] Jawaharlal Nehru Technol Univ, Dept Chem, Hyderabad 500085, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 12期
关键词
total synthesis; heterocycles; vicarious aromatic substitution; cyclization; alkylation; SPONGE AAPTOS-AAPTOS; ALKALOIDS; DESIGN; POTENT; INHIBITORS; DISCOVERY; OXIDATION; EFFICIENT;
D O I
10.1055/s-0036-1588752
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic sequence to the benzonaphthyridinone framework is described. The key step is a one-pot, base-catalyzed vicarious nucleophilic substitution followed by ring closure. Additionally, the synthesis represents the application of a vicarious nucleophilic substitution in the total synthesis of a cytotoxic aaptamine derivative.
引用
收藏
页码:2768 / 2774
页数:7
相关论文
共 50 条
  • [1] Azine Dearomatization in Natural Product Total Synthesis
    Knight, Brian J.
    Grigolo, Thiago A.
    Tolchin, Zachary A.
    Smith, Joel M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2025, 31 (19)
  • [2] First total synthesis of the marine natural product viscosamine
    Timm, Christoph
    Koeck, Matthias
    SYNTHESIS-STUTTGART, 2006, 15 (15): : 2580 - 2584
  • [3] The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate
    Kesic, Jelena
    Kovacevic, Ivana
    Popsavin, Mirjana
    Benedekovic, Goran
    Rodic, Marko V.
    Kojic, Vesna
    Popsavin, Velimir
    BIOORGANIC CHEMISTRY, 2022, 128
  • [4] Total Synthesis of Aaptamine, Demethyloxyaaptamine, and Their 3-Alkylamino Derivatives
    Gao, Yuan
    Yang, Fan
    Sun, Fan
    Liu, Lei
    Liu, Bo
    Wang, Shu-Ping
    Cheng, Chun-Wei
    Liao, Hongze
    Lin, Hou-Wen
    ORGANIC LETTERS, 2019, 21 (05) : 1430 - 1433
  • [5] Total Synthesis of the Anticancer Marine Natural Product Mycalol
    Rao, K. Nageswara
    Kumar, Katragunta
    Ghosh, Subhash
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) : 398 - 412
  • [6] Total Synthesis of Polyene Natural Product Dihydroxerulin by Mild Organocatalyzed Dehydrogenation of Alcohols
    Xie, Hexin
    Zhang, Shilei
    Li, Hao
    Zhang, Xinshuai
    Zhao, Sihan
    Xu, Zian
    Song, Xixi
    Yu, Xinhong
    Wang, Wei
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (08) : 2230 - 2234
  • [7] Efficiency in Natural Product Total Synthesis
    Zografos, Alexandros L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2738 - 2739
  • [8] Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents
    Shen, Li
    Xie, Nan
    Yang, Bo
    Hu, Yongzhou
    Zhang, Yongmin
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 : 807 - 817
  • [9] Total Synthesis of Natural Product Luxenchalcone
    Zhang Ying-Peng
    Zhang Wei-Na
    Yang Yun-Shang
    Qiao Ming
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2013, 34 (12): : 2734 - 2737
  • [10] First Total Synthesis of Oxirapentyn D, a Highly Oxidized Chromene Natural Product
    Sakai, Takahiro
    Suzuki, Keisuke
    Ohmori, Ken
    SYNLETT, 2018, 29 (10) : 1351 - 1357