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
  • [21] Total Synthesis of the Antifungal Natural Product Mollisin
    Schwolow, Sonja
    Kunz, Horst
    Rheinheimer, Joachim
    Opatz, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (29) : 6519 - 6524
  • [22] Total Synthesis of an Oxepine Natural Product, (±)-Janoxepin
    Doveston, Richard G.
    Steendam, Rene
    Jones, Stuart
    Taylor, Richard J. K.
    ORGANIC LETTERS, 2012, 14 (04) : 1122 - 1125
  • [23] Total Synthesis of the Flavonoid Natural Product Houttuynoid A
    Jian, Jie
    Fan, Jilin
    Yang, Hui
    Lan, Ping
    Li, Manmei
    Liu, Peijun
    Gao, Hao
    Sun, Pinghua
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (02): : 371 - 377
  • [24] Total Synthesis of (+)-Petromyroxol, a Marine Natural Product
    Gahalawat, Suraksha
    Garg, Yuvraj
    Pandey, Satyendra Kumar
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1025 - 1029
  • [25] First total synthesis of eudistalbin A
    Zhang, Pu Yong
    Wang, Jun Lei
    Wan, Sheng Biao
    Jiang, Tao
    CHINESE CHEMICAL LETTERS, 2010, 21 (08) : 889 - 891
  • [26] A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine, a potent anticancer agent
    Lin, Song-Bo
    Wang, Wan-Wan
    Meng, Jin-Peng
    Li, Xi-Wang
    Wu, Jun
    Sun, Xiao-Ling
    TETRAHEDRON LETTERS, 2019, 60 (51)
  • [27] Total Synthesis of Limonin, a Personal Story on Natural Product Synthesis
    Yamashita, Shuji
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (05) : 514 - 517
  • [28] A Chemoenzymatic and Fully Stereocontrolled Total Synthesis of the Antibacterial Natural Product (-)-Platencin
    Chang, Ee Ling
    Schwartz, Brett D.
    Draffan, Alistair G.
    Banwell, Martin G.
    Willis, Anthony C.
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (02) : 427 - 439
  • [29] Total Synthesis of Laulimalide: Assembly of the Fragments and Completion of the Synthesis of the Natural Product and a Potent Analogue
    Trost, Barry M.
    Amans, Dominique
    Seganish, W. Michael
    Chung, Cheol K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) : 2961 - 2971
  • [30] The first stereoselective synthesis of the natural product, rotenone
    Georgiou, Kathy Hadje
    Pelly, Stephen C.
    de Koning, Charles B.
    TETRAHEDRON, 2017, 73 (07) : 853 - 858
12345