Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

被引:9
|
作者
Park, Sooyoung [1 ]
Kim, Jin-Hee [2 ]
Kim, Seok-Ho [3 ,4 ]
Shin, Dongyun [1 ]
机构
[1] Gachon Univ, Coll Pharm, Incheon, South Korea
[2] Yonsei Univ, Coll Pharm, Incheon, South Korea
[3] CHA Univ, Coll Pharm, Dept Pharm, Pocheon Si, South Korea
[4] CHA Univ, Inst Pharmaceut Sci, Pocheon Si, South Korea
来源
FRONTIERS IN CHEMISTRY | 2020年 / 8卷
基金
新加坡国家研究基金会;
关键词
transition metal; arylnaphthalene; catalysis; lignan; synthesis; lactone; CATALYZED 2+2+2 COCYCLIZATION; JUSTICIDIN-E; TAIWANIN-C; ANTIVIRAL ACTIVITY; COUPLING REACTIONS; CYCLIZATION; ARYNES; CELLS; ACIDS; PODOPHYLLOTOXIN;
D O I
10.3389/fchem.2020.00628
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Arylnaphthalene lignan lactones belong to a class of natural lignans, and more than 60 analogs have been isolated. Their pharmacological activities as well as unique structural features have attracted considerable attention from medicinal and synthetic chemists. Since the first synthesis in 1895, many synthetic methodologies with ionic or pericyclic reaction mechanisms have been reported. Transition metal catalysts sometimes provide exceptional synthetic versatility for the syntheses of natural compounds. Recently, transition metal-mediated methodologies were investigated for the construction of basic scaffolds of arylnaphthalene lignan lactones. Five kinds of transition metal catalysts containing gold, manganese, nickel, palladium, and silver have been explored. Most of the metal catalysts successfully created arylnaphthalene lactones by intermolecular or intramolecular annulative cyclization. In this review, all reports of transition metal-mediated annulative construction of arylnaphthalene lignan lactones were compiled, and synthetic approaches, mechanistic aspects, and successful applications were discussed.
引用
收藏
页数:15
相关论文
共 50 条
  • [21] Transition metal-mediated catalytic properties of gold nanoclusters in aerobic alcohol oxidation
    Zhang, Chaolei
    Chen, Yongdong
    Wang, Hong
    Li, Zhimin
    Zheng, Kai
    Li, Shujun
    Li, Gao
    NANO RESEARCH, 2018, 11 (04) : 2139 - 2148
  • [22] Recent Advances in Transition Metal Mediated Synthetic Approaches to Quinoline Derivatives
    Tabassum, Rukhsana
    Ashfaq, Muhammad
    Oku, Hiroyuki
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (09) : 669 - 686
  • [23] A narrative review: progress in transition metal-mediated bioorthogonal catalysis for the treatment of solid tumors
    Wan, Xiaotian
    Zhang, Yiwen
    Nie, Yueli
    Zhang, Keyong
    Jin, Ze
    Zhang, Zhikun
    Gan, Lu
    Liu, Xiyu
    He, Jian
    TRANSLATIONAL CANCER RESEARCH, 2023, 12 (08) : 2181 - 2196
  • [24] Synthesis of Fused Lactones through Transition-Metal-Catalyzed peri C-H Functionalization
    Nishida, Ayako
    Inai, Yasuhito
    Usuki, Yoshinosuke
    Satoh, Tetsuya
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (05)
  • [25] Recent advances in bidentate bis(N-heterocyclic carbene) transition metal complexes and their applications in metal-mediated reactions
    Gardiner, Michael G.
    Ho, Curtis C.
    COORDINATION CHEMISTRY REVIEWS, 2018, 375 : 373 - 388
  • [26] Transition Metal-Catalyzed Intermolecular Cascade C-H Activation/Annulation Processes for the Synthesis of Polycycles
    Song, Liangliang
    Van der Eycken, Erik V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (01) : 121 - 144
  • [27] Expanding Transition Metal-Mediated Bioorthogonal Decaging to Include C-C Bond Cleavage Reactions
    Dal Forno, Gean M.
    Latocheski, Eloah
    Machado, Ana Beatriz
    Becher, Julie
    Dunsmore, Lavinia
    St John, Albert L.
    Oliveira, Bruno L.
    Navo, Claudio D.
    Jimenez-Oses, Gonzalo
    Fior, Rita
    Domingos, Josiel B.
    Bernardes, Goncalo J. L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (19) : 10790 - 10799
  • [28] Metal-Mediated Synthesis of 1,4-Di-tert-butyl-1,4-azaborine
    Braunschweig, Holger
    Damme, Alexander
    Jimenez-Halla, J. Oscar C.
    Pfaffinger, Bernd
    Radacki, Krzysztof
    Wolf, Justin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (40) : 10034 - 10037
  • [29] The application of transition metal catalysis for selective cyclocarbonylation reactions. Synthesis of lactones and lactams
    El Ali, B
    Alper, H
    SYNLETT, 2000, (02) : 161 - 171
  • [30] Synthesis of functional carbocycles and heterocycles via transition-metal-catalyzed annulation or homocoupling of difluorocyclopropenes
    Wang, Ting
    Chen, Jian
    Shi, Yue-Sen
    Liu, Xue-Xin
    Guo, Li
    Wu, Yong
    TETRAHEDRON LETTERS, 2022, 99