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
来源：
SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 7-9期
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
  • [41] Palladium-catalyzed cyclization reactions.
    Mutter, R
    Wills, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U195 - U195
  • [42] Palladium-catalyzed cyclization of enediynes to benzopyranones
    Chang, Wei-Ren
    Lo, Yu-Hsiang
    Lee, Chia-Ying
    Wu, Ming-Jung
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1248 - 1252
  • [43] Palladium-Catalyzed Cyclization of Alkenes with Organohalides
    Chu, Xue-Qiang
    Liu, Dan
    Xing, Zhen-Hua
    Xu, Xiao-Ping
    Ji, Shun Jun
    ORGANIC LETTERS, 2016, 18 (04) : 776 - 779
  • [44] Palladium-Catalyzed Carbonylative Cyclization of Azoarenes
    Wang, Zechao
    Yin, Zhiping
    Zhu, Fengxiang
    Li, Yahui
    Wu, Xiao-Feng
    CHEMCATCHEM, 2017, 9 (19) : 3637 - 3640
  • [45] Palladium-catalyzed bismetallative cyclization of enynes
    Mori, M
    Hirose, T
    Wakamatsu, H
    Imakuni, N
    Sato, Y
    ORGANOMETALLICS, 2001, 20 (10) : 1907 - 1909
  • [46] Synthesis of Biindolyls via Palladium-Catalyzed Reactions
    Duong, Hung A.
    Chua, Sheena
    Huleatt, Paul B.
    Chai, Christina L. L.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22): : 9177 - 9180
  • [47] Synthesis of ikimine a via palladium-catalyzed coupling
    Larock, RC
    Dong, XY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 288 - ORGN
  • [48] Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations
    Wu, Xiao-Feng
    Neumann, Helfried
    Beller, Matthias
    CHEMICAL REVIEWS, 2013, 113 (01) : 1 - 35
  • [49] Solid-phase synthesis of skeletally diverse benzofused sultams via palladium-catalyzed cyclization
    Chen, Wenteng
    Li, Zhi
    Ou, Lili
    Giulianott, Marc A.
    Houghten, Richard A.
    Yu, Yongping
    TETRAHEDRON LETTERS, 2011, 52 (13) : 1456 - 1458
  • [50] Synthesis of tetracyclic 5-azaindole analogues by palladium-catalyzed sequential annulation
    Sung, ND
    Yang, OK
    Kang, SS
    Yum, EK
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (09) : 1351 - 1354
12345