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] First total synthesis of the cytotoxic marine natural product aplysiapyranoid C.
    Jung, ME
    Fahr, BT
    DAmico, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 319 - ORGN
  • [2] The first total synthesis of the natural product angoluvarin
    Nutaitis, Charles F.
    TETRAHEDRON LETTERS, 2010, 51 (41) : 5497 - 5499
  • [3] THE TOTAL SYNTHESIS OF AAPTAMINE
    PELLETIER, JC
    CAVA, MP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 188 (AUG): : 63 - ORGN
  • [4] An Evaluation of the Cytotoxic Effect of the Natural Product Aaptamine Against t(4;11) Leukemias
    Sinha, Chandrima
    Bowling, John
    Seth, Aman
    Ju, Bensheng
    Kahali, Bhaskar
    Hamann, Mark
    Cunningham, Lea C.
    BLOOD, 2016, 128 (22)
  • [5] First total synthesis of the marine natural product viscosamine
    Timm, Christoph
    Koeck, Matthias
    SYNTHESIS-STUTTGART, 2006, 15 (15): : 2580 - 2584
  • [6] Towards the total synthesis of the potent cytotoxic marine natural product dichlorolissoclimide
    Jung, ME
    Kalin, T
    Gomez, AV
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 283 - ORGN
  • [7] A NEW TOTAL SYNTHESIS OF AAPTAMINE
    ANDREW, RG
    RAPHAEL, RA
    TETRAHEDRON, 1987, 43 (21) : 4803 - 4816
  • [8] First total synthesis of chapecoderin A: absolute configuration of the natural product
    Hagiwara, H
    Takeuchi, F
    Hoshi, T
    Suzuki, T
    Ando, M
    TETRAHEDRON LETTERS, 2001, 42 (43) : 7629 - 7631
  • [9] 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
  • [10] STEREOCONTROLLED SYNTHESIS OF MARINE CYTOTOXIC NATURAL PRODUCT
    ICHIKAWA, Y
    NIPPON NOGEIKAGAKU KAISHI-JOURNAL OF THE JAPAN SOCIETY FOR BIOSCIENCE BIOTECHNOLOGY AND AGROCHEMISTRY, 1991, 65 (11): : 1627 - 1634