Total synthesis of the marine pyrroloiminoquinone alkaloid tsitsikammamine A

被引：21
作者：
Rives, Arnaud [1 ]
Delaine, Tamara [1 ]
Legentil, Laurent [1 ]
Delfourne, Evelyne [1 ]
机构：
[1] Univ Toulouse 3, CNRS, UMR 5068, Lab Synth & Physicochim Mol Interet Biol, F-31062 Toulouse 9, France
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 10期
关键词：
Synthesis; Marine alkaloid; Pyrroloiminoquinone; Tsitsikammamine; PYRROLOQUINOLINE ALKALOIDS; BIOLOGICAL EVALUATION; NATURAL-PRODUCTS; ANALOGS; WAKAYIN; MAKALUVAMINES; INHIBITION; SPONGES;
D O I：
10.1016/j.tetlet.2008.12.078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise route to the marine pyrroloiminoquinone alkaloid tsitsikammamine A and a regioisomer was developed. The synthesis was based on a Michael reaction between the indole dione 6 and 2'-amino-1-(4-methoxyphenyl)ethanol. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1128 / 1130
页数：3
相关论文
共 50 条
  • [21] Enantioselective total synthesis of the polycyclic guanidine-containing marine alkaloid (-)-batzelladine D
    Evans, P. Andrew
    Qin, Jun
    Robinson, John E.
    Bazin, Berangere
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) : 7417 - 7419
  • [22] A Novel Marine Natural Product Derived Pyrroloiminoquinone with Potent Activity against Skin Cancer Cells
    Cowan, Jaden
    Shadab, Mohammad
    Nadkarni, Dwayaja H.
    Kailash, K. C.
    Velu, Sadanandan E.
    Yusuf, Nabiha
    MARINE DRUGS, 2019, 17 (08)
  • [23] IDO1 and TDO inhibitory evaluation of analogues of the marine pyrroloiminoquinone alkaloids: Wakayin and Tsitsikammamines
    Levy, Thomas
    Marchand, Laura
    Stroobant, Vincent
    Pilotte, Luc
    Van den Eynde, Benoit
    Rodriguez, Frederic
    Delfourne, Evelyne
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 40
  • [24] An efficient and concise total synthesis of the antimalarial alkaloid quindoline
    Bastos, Dayse dos S.
    Silva, Anna C.
    Albert, Andre L. M.
    Barros, Wesley M. R.
    Slana, Glaucia B. C. A.
    Cardoso, Jari N.
    Lopes, Rosangela S. C.
    Lopes, Claudio C.
    TETRAHEDRON LETTERS, 2013, 54 (24) : 3144 - 3146
  • [25] Design, Synthesis and Bioactivity Study of Marine Alkaloid Neobacillamide—A Derivatives
    Jiali Wang
    Maowei Li
    Xiao Zhang
    Zhijin Zhang
    Yang Liu
    Lu Liu
    Ruijuan Yin
    Tao Jiang
    Journal of Ocean University of China, 2023, 22 : 790 - 800
  • [26] Total synthesis of the indolizidinium alkaloid ficuseptine
    Bracher, F
    Daab, J
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (14) : 2288 - 2291
  • [27] Total Synthesis of the Akuammiline Alkaloid Strictamine
    Liu, Xiaoyu
    Xiao, Tao
    Qinl, Yong
    PROGRESS IN CHEMISTRY, 2018, 30 (05) : 578 - 585
  • [28] Total synthesis of the cytotoxic alkaloid luotonin A
    Wang, HS
    Ganesan, A
    TETRAHEDRON LETTERS, 1998, 39 (49) : 9097 - 9098
  • [29] Evaluation of the Antioxidant Activity of the Marine Pyrroloiminoquinone Makaluvamines
    Alonso, Eva
    Alvarino, Rebeca
    Leiros, Marta
    Tabudravu, Jioji N.
    Feussner, Klaus
    Dam, Miriam A.
    Rateb, Mostafa E.
    Jaspars, Marcel
    Botana, Luis M.
    MARINE DRUGS, 2016, 14 (11)
  • [30] Total synthesis of a piperidine alkaloid, microcosamine A
    Reddy, Chada Raji
    Latha, Bellamkonda
    Warudikar, Kamalkishor
    Singarapu, Kiran Kumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (01) : 251 - 258
12345