Synthesis of isagarin, a tetracyclic naphthoquinone via a palladium-catalyzed cyclization

被引:8
|
作者
Ploysuk, Chatchawan [1 ]
Kongkathip, Boonsong [1 ]
Kongkathip, Ngampong [1 ]
机构
[1] Kasetsart Univ, Fac Sci, Natl Prod & Organ Synth Res Unit, Dept Chem, Bangkok 10900, Thailand
关键词
isagarin; naphthoquinone; palladium; synthesis; wacker;
D O I
10.1080/00397910701227432
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of isagarin (2) has been accomplished in five steps with 24.1% overall yield from 2-bromonaphthoquinone (6). The key step is a palladium-catalyzed cyclization to form a bicyclic ketal ring.
引用
收藏
页码:1463 / 1471
页数:9
相关论文
共 50 条
  • [31] SYNTHESIS OF SUBSTITUTED FURANS BY PALLADIUM-CATALYZED CYCLIZATION OF ACETYLENIC KETONES
    FUKUDA, Y
    SHIRAGAMI, H
    UTIMOTO, K
    NOZAKI, H
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20): : 5816 - 5819
  • [32] Total Synthesis of Cyclopiamide A Using Palladium-Catalyzed Domino Cyclization
    Park, Sunhwa
    Shin, Kye Jung
    Seo, Jae Hong
    MOLECULES, 2020, 25 (21):
  • [33] Synthesis of isoquinolines by palladium-catalyzed cyclization, followed by a Heck reaction
    Huang, QH
    Larock, RC
    TETRAHEDRON LETTERS, 2002, 43 (19) : 3557 - 3560
  • [34] Palladium-catalyzed asymmetric dearomative cyclization in natural product synthesis
    Wang, Zhuo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (23) : 4354 - 4370
  • [35] Synthesis of dithienothiophenes, cyclopentadithiophene and silacyclopentadithiophenes using palladium-catalyzed cyclization
    Iyoda, M
    Miura, M
    Sasaki, S
    Kabir, SMH
    Kuwatani, Y
    Yoshida, M
    TETRAHEDRON LETTERS, 1997, 38 (26) : 4581 - 4582
  • [36] Synthesis of dimethyl gloiosiphone a by way of palladium-catalyzed domino cyclization
    Doi, Takayuki
    Iijima, Yusuke
    Takasaki, Masaru
    Takahashi, Takashi
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10): : 3667 - 3671
  • [37] Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins
    Liao, Jianhua
    Fan, Lianfeng
    Guo, Wei
    Zhang, Zhenming
    Li, Jiawei
    Zhu, Chuanle
    Ren, Yanwei
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC LETTERS, 2017, 19 (05) : 1008 - 1011
  • [38] Palladium-Catalyzed Cyclization of Propargylic Compounds
    Guo, Li-Na
    Duan, Xin-Hua
    Liang, Yong-Min
    ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (02) : 111 - 122
  • [39] A NOVEL PALLADIUM-CATALYZED REDUCTIVE CYCLIZATION
    TROST, BM
    WALCHLI, R
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3487 - 3488
  • [40] Palladium-Catalyzed Asymmetric Intermolecular Cyclization
    Hu, Jian
    Hirao, Hajime
    Li, Yongxin
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8676 - 8680