Synthesis of phenanthridine skeletal Amaryllidaceae alkaloids

被引：38
|
作者：
Fan-Chiang, Tai-Ting [1 ]
Wang, Hung-Kai [1 ]
Hsieh, Jen-Chieh [1 ]
机构：
[1] Tamkang Univ, Dept Chem, New Taipei 25137, Taiwan
来源：
TETRAHEDRON | 2016年 / 72卷 / 36期
关键词：
Amaryllidaceae alkaloid; DNA topoisomerase I; Suzuki coupling; Ullmann coupling; SNAr; COPPER-CATALYZED ANNULATION; VINYL GRIGNARD-REAGENTS; CONSTITUENTS; DERIVATIVES; LYCORINE; BULBS;
D O I：
10.1016/j.tet.2016.07.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Strategies for the synthesis of Amaryllidaceae alkaloids, including crinasiadine, trisphaeridine, bicolorine, N-methylcrinasiadine, 5,6-dihydrobicolorine, galanthindole, lycosinine A and lycosinine B were reported. Investigation of optionally synthetic routes to approach bicolorine, 5,6-dihydrobicolorine, trisphaeridine and N-methylcrinasiadine were demonstrated as well. In addition, three structurally related alkaloids galanthindole, lycosinine A and lycosinine B were concisely prepared by using Suzuki coupling reaction as the key step. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5640 / 5645
页数：6
相关论文
共 50 条
  • [21] Cytotoxic Agents of the Crinane Series of Amaryllidaceae Alkaloids
    Nair, Jerald J.
    Bastida, Jaume
    Viladomat, Francesc
    van Staden, Johannes
    NATURAL PRODUCT COMMUNICATIONS, 2012, 7 (12) : 1677 - 1688
  • [22] Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine
    Yang, Lijuan
    Wang, Xuequan
    Pan, Zhiqiang
    Zhou, Ming
    Chen, Wen
    Yang, Xiaodong
    SYNLETT, 2011, (02) : 207 - 210
  • [23] Pancratium canariense as an Important Source of Amaryllidaceae Alkaloids
    Cedron, Juan C.
    Oberti, Juan C.
    Estevez-Braun, Ana
    Ravelo, Angel G.
    Del Arco-Aguilar, Marcelino
    Lopez, Matias
    JOURNAL OF NATURAL PRODUCTS, 2009, 72 (01): : 112 - 116
  • [24] Alkaloids and triterpenoids from Ammocharis coranica (Amaryllidaceae)
    Koorbanally, N
    Mulholland, DA
    Crouch, N
    PHYTOCHEMISTRY, 2000, 54 (01) : 93 - 97
  • [25] Cytotoxic tazettine alkaloids of the plant family Amaryllidaceae
    Nair, Jerald J.
    Van Staden, Johannes
    SOUTH AFRICAN JOURNAL OF BOTANY, 2021, 136 : 147 - 156
  • [26] In vitro Antiplasmodial Activities of Alkaloids Isolated from Roots of Worsleya procera (Lem.) Traub (Amaryllidaceae)
    Gonring-Salarini, Karla L.
    Conti, Raphael
    de Andrade, Jean Paulo
    Borges, Barbara Juliana P.
    Aguiar, Anna Caroline C.
    de Souza, Juliana O.
    Zanini, Camila L.
    Oliva, Glaucius
    Tenorio, Juan Carlos
    Ellena, Javier
    Bastida, Jaume
    Guido, Rafael V. C.
    Borges, Warley de S.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2019, 30 (08) : 1624 - 1633
  • [27] South African Amaryllidaceae part VIII -: Alkaloids from Crinum macowanii
    Nair, JJ
    Machocho, AK
    Campbell, WE
    Brun, R
    Viladomat, F
    Codina, C
    Bastida, J
    PHYTOCHEMISTRY, 2000, 54 (08) : 945 - 950
  • [28] IMPROVED HPLC METOD FOR THE DETERMINATION OF AMARYLLIDACEAE ALKALOIDS
    Ivanov, I.
    Berkov, S.
    Pavlov, A.
    BIOTECHNOLOGY & BIOTECHNOLOGICAL EQUIPMENT, 2009, 23 : 809 - 813
  • [29] The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids
    Paulo de Andrade, Jean
    Giordani, Raquel B.
    Torras-Claveria, Laura
    Belen Pigni, Natalia
    Berkov, Strahil
    Font-Bardia, Merce
    Calvet, Teresa
    Konrath, Eduardo
    Bueno, Kelly
    Sachett, Liana G.
    Dutilh, Julie H.
    Borges, Warley de Souza
    Viladomat, Francesc
    Henriques, Amelia T.
    Nair, Jerald J.
    Zuanazzi, Jose Angelo S.
    Bastida, Jaume
    PHYTOCHEMISTRY REVIEWS, 2016, 15 (01) : 147 - 160
  • [30] Cell cycle modulatory effects of Amaryllidaceae alkaloids
    Nair, Jerald J.
    van Staden, Johannes
    LIFE SCIENCES, 2018, 213 : 94 - 101
12345