Recent developments in the synthesis of zoanthamine alkaloids

被引:6
|
作者
Yoshimura, Fumihiko [1 ]
Tanino, Keiji [1 ]
Miyashita, Masaaki [1 ]
机构
[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
关键词
Zoanthamine alkaloids; Total synthesis; Quaternary asymmetric carbon atom; Aminoacetal; MICHAEL REACTION CASCADE; ABC-RING; MARINE ZOANTHID; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; CARBOCYCLIC CORE; NORZOANTHAMINE; CYCLIZATION; CONSTRUCTION;
D O I
10.1016/j.tetlet.2014.03.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review provides a compilation of the most recent synthetic approaches and total syntheses of zoanthamine alkaloids, which are structurally unique heptacyclic marine natural products that display a range of interesting biological activities. This review is focused on synthetic methodologies for the construction of the three adjacent quaternary asymmetric carbon atoms on the cyclohexane ring (C-ring) of these compounds. The literature covered in this review dates from 2008 to the end of 2013. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-SA license
引用
收藏
页码:2895 / 2903
页数:9
相关论文
共 50 条
  • [1] Chemical Synthesis of Zoanthamine Alkaloids
    Yoshimura, Fumihiko
    Tanino, Keiji
    Miyashita, Masaaki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2013, 71 (02) : 124 - 135
  • [2] Total Synthesis of Zoanthamine Alkaloids
    Yoshimura, Fumihiko
    Tanino, Keiji
    Miyashita, Masaaki
    ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (05) : 746 - 755
  • [3] Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids
    Fischer, Derek
    Nguyen, Thong X.
    Trzoss, Lynnie
    Dakanali, Marianna
    Theodorakis, Emmanuel A.
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4920 - 4923
  • [4] Synthetic Studies of the Zoanthamine Alkaloids: Total Synthesis of Zoanthenol Based on an Isoaromatization Strategy
    Yoshimura, Fumihiko
    Takahashi, Yu
    Tanino, Keiji
    Miyashita, Masaaki
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (03) : 922 - 931
  • [5] Synthetic Studies of the Zoanthamine Alkaloids: The Total Syntheses of Norzoanthamine and Zoanthamine
    Yoshimura, Fumihiko
    Sasaki, Minoru
    Hattori, Izumi
    Komatsu, Kei
    Sakai, Mio
    Tanino, Keiji
    Miyashita, Masaaki
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (27) : 6626 - 6644
  • [6] The biology and chemistry of the zoanthamine alkaloids
    Behenna, Douglas C.
    Stockdill, Jennifer L.
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) : 2365 - 2386
  • [7] Developments in the Synthesis of Hasubanan Alkaloids
    Ikonnikova, Viktoria A.
    Baranov, Mikhail S.
    Mikhaylov, Andrey A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (31)
  • [8] Recent Advances in the Synthesis of Morphine and Related Alkaloids
    Chida, Noritaka
    CHEMISTRY OF OPIOIDS, 2011, 299 : 1 - 28
  • [9] Zoanthamine Alkaloids from the Zoantharian Zoanthus cf. pulchellus and Their Effects in Neuroinflammation
    Guillen, Paul O.
    Gegunde, Sandra
    Jaramillo, Karla B.
    Alfonso, Amparo
    Calabro, Kevin
    Alonso, Eva
    Rodriguez, Jenny
    Botana, Luis M.
    Thomas, Olivier P.
    MARINE DRUGS, 2018, 16 (07):
  • [10] Total Synthesis of the Zoanthamine Alkaloid
    M.Miyashita
    复旦学报(自然科学版), 2005, (05) : 171 - 172