Synthetic Approaches to Tetracyclic Pyrrole Imidazole Marine Alkaloids

被引:0
作者
Imaoka, Takuya [1 ]
Iwata, Makoto [1 ]
Akimoto, Takafumi [1 ]
Nagasawa, Kazuo [1 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Biotechnol & Life Sci, Koganei, Tokyo 1848588, Japan
关键词
Pyrrole-imidazole alkaloid; Total synthesis; Oroidin; Phakellin; Phakellstatin; N; N-aminal; PUMMERER REACTION CHEMISTRY; (+/-)-DIBROMOPHAKELLSTATIN; (+)-DIBROMOPHAKELLSTATIN; DIBROMOPHAKELLSTATIN;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Oroidin derived, pyrrole imidazole marine alkaloids (PIAs) are attractive targets for synthetic organic chemists because of their structural complexity and diversity, as well as their interesting biological activities. A number of efforts have been carried out to develop strategies for the synthesis of these natural products. Members of PIAs (eg., 2-7), which contain tetracyclic ring systems possessing characteristic cyclic guanidine or urea moieties, show significant biological activities including anticancer activity and agonistic activity against the adrenoceptor. In this review, investigations of the total synthesis of the representative tetracyclic PIAs, dibromophakellin (2) and dibromophakellstatin (3), are described.
引用
收藏
页码:961 / 964
页数:4
相关论文
共 50 条
  • [21] Total synthesis of tricyclic marine alkaloids
    Kibayashi, Chihiro
    Aoyagi, Sakae
    Abe, Hideki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (08) : 805 - 819
  • [22] Total synthesis of a marine imidazole alkaloid, clathridine A
    Ohta, S
    Tsuno, N
    Maeda, K
    Nakamura, S
    Taguchi, N
    Yamashita, M
    Kawasaki, I
    TETRAHEDRON LETTERS, 2000, 41 (23) : 4623 - 4627
  • [23] Total Synthesis of Two Pyrrole Spiroketal Alkaloids: Pollenopyrroside A and Capparisine B
    Cao, Zhi
    Li, Yueqing
    Wang, Shisheng
    Guo, Xiuhan
    Wang, Liu
    Zhao, Weijie
    SYNLETT, 2015, 26 (07) : 921 - 926
  • [24] Synthesis of 7-15N-Oroidin and Evaluation of Utility for Biosynthetic Studies of Pyrrole-Imidazole Alkaloids by Microscale 1H-15N HSQC and FTMS
    Wang, Yong-Gang
    Morinaka, Brandon I.
    Reyes, Jeremy Chris P.
    Wolff, Jeremy J.
    Romo, Daniel
    Molinski, Tadeusz F.
    JOURNAL OF NATURAL PRODUCTS, 2010, 73 (03): : 428 - 434
  • [25] Total synthesis of the marine alkaloids Caulibugulones A and D
    Prakash, K. S.
    Nagarajan, Rajagopal
    TETRAHEDRON, 2015, 71 (05) : 801 - 804
  • [26] New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids
    Plodek, Alois
    Bracher, Franz
    MARINE DRUGS, 2016, 14 (02):
  • [27] Synthesis of the diazatricyclic core of the marine alkaloids madangamines
    Yamazaki, N
    Kusanagi, T
    Kibayashi, C
    TETRAHEDRON LETTERS, 2004, 45 (34) : 6509 - 6512
  • [28] Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View
    Liu, Xiao-Yu
    Qin, Yong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1010 - 1019
  • [29] Synthetic Studies toward Dimeric Indole Alkaloids Based on Convergent Synthetic Strategy
    Ueda, Hirofumi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2020, 68 (02) : 117 - 128
  • [30] Recent Advances in the Total Synthesis of Aspidosperma and Kopsia Alkaloids Using Tetracyclic Pyridocarbazoles as Versatile Building Blocks
    Wang, Nengzhong
    Xiao, Xiao
    Liu, Cheng-Xiong
    Yao, Hui
    Huang, Nianyu
    Zou, Kun
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (15) : 2479 - 2501