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] Total Synthesis of Zoanthamine Alkaloids
    Yoshimura, Fumihiko
    Tanino, Keiji
    Miyashita, Masaaki
    ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (05) : 746 - 755
  • [2] Chemical Synthesis of Zoanthamine Alkaloids
    Yoshimura, Fumihiko
    Tanino, Keiji
    Miyashita, Masaaki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2013, 71 (02) : 124 - 135
  • [3] 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
  • [4] 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
  • [5] Recent developments in the synthesis of biologically active indole alkaloids
    Lobo, AM
    Prabhakar, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (03) : 429 - 436
  • [6] 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
  • [7] A SYNTHETIC APPROACH TO THE ZOANTHAMINE ALKALOIDS
    TANNER, D
    ANDERSSON, PG
    TEDENBORG, L
    SOMFAI, P
    TETRAHEDRON, 1994, 50 (30) : 9135 - 9144
  • [8] RECENT DEVELOPMENTS IN COLCHICUM ALKALOIDS
    BROSSI, AR
    TRENDS IN PHARMACOLOGICAL SCIENCES, 1983, 4 (08) : 327 - 328
  • [9] RECENT DEVELOPMENTS IN ISOQUINOLINE ALKALOIDS
    SHAMMA, M
    YAO, SY
    NUGENT, JF
    MONIOT, JL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1972, : 12 - &
  • [10] Advances in the syntheses of zoanthamine alkaloids.
    Patnaik, S
    Williams, DR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U128 - U128