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
  • [1] Synthesis of Arylnaphthalene Lignan Lactones
    Meng, Jin
    Du, Liyue
    Guo, Liucheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (11) : 2723 - 2728
  • [2] TRANSITION METAL-MEDIATED SYNTHESIS OF OXAZOLES
    Bresciani, Stefano
    Tomkinson, Nicholas C. O.
    HETEROCYCLES, 2014, 89 (11) : 2479 - 2543
  • [3] Synthesis and antiproliferative activity of derivatives of the phyllanthusmin class of arylnaphthalene lignan lactones
    Woodard, John L.
    Huntsman, Andrew C.
    Patel, Pratiq A.
    Chai, Hee-Byung
    Kanagasabai, Ragu
    Karmahapatra, Soumendrakrishna
    Young, Alexandria N.
    Ren, Yulin
    Cole, Malcolm S.
    Herrera, Denisse
    Yalowich, Jack C.
    Kinghorn, A. Douglas
    Burdette, Joanna E.
    Fuchs, James R.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (09) : 2354 - 2364
  • [4] Transition metal-mediated routes to cyclopentenones
    Gibson, SE
    Lewis, SE
    Mainolfi, N
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) : 3873 - 3890
  • [5] Recent advances in metal-mediated synthesis of substituted furans
    Li, LT
    Ma, SM
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2000, 20 (05) : 701 - 711
  • [6] Metal-Catalyzed and Metal-Mediated Approaches to the Synthesis and Functionalization of Tetramic Acids
    Matiadis, Dimitris
    CATALYSTS, 2019, 9 (01)
  • [7] Transition Metal-mediated Reactions in Biological Media
    Martinez-Calvo, Miguel
    Mascarenas, Jose L.
    CHIMIA, 2018, 72 (11) : 791 - 801
  • [8] Transition metal-mediated separation of isomeric pneumocandins by capillary electrochromatography
    Hoffman, MJ
    Dovletoglou, A
    HRC-JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY, 1999, 22 (06): : 309 - 314
  • [9] Recent Advances of Transition Metal-Mediated Oxidative Radical Reactions in Total Synthesis of Indole Alkaloids
    Liang, Kangjiang
    Xia, Chengfeng
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (03) : 255 - 270
  • [10] Mechanistic insights into transition metal-mediated bioorthogonal uncaging reactions
    Latocheski, Eloah
    Dal Forno, Gean M.
    Ferreira, Thuany M.
    Oliveira, Bruno L.
    Bernardes, Goncalo J. L.
    Domingos, Josiel B.
    CHEMICAL SOCIETY REVIEWS, 2020, 49 (21) : 7710 - 7729