Total Synthesis of Bongkrekic Acid via Sequential Suzuki-Miyaura Coupling Reactions

被引:24
|
作者
Kanematsu, Makoto [1 ]
Shindo, Mitsuru [2 ]
Yoshida, Masahiro [1 ]
Shishido, Kozo [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
[2] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan
来源
SYNTHESIS-STUTTGART | 2009年 / 17期
关键词
apoptosis; conjugated diene; Suzuki-Miyaura coupling; palladium; bongkrekic acid; MITOCHONDRIAL PERMEABILITY TRANSITION; (E)-1-ALKENYLBORONIC ESTERS; STEREOSPECIFIC SYNTHESIS; CATALYTIC AMOUNT; TRANSFORMATION; ALDEHYDES; APOPTOSIS; OXIDATION; REAGENTS; OLEFINS;
D O I
10.1055/s-0029-1216928
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient total synthesis of (+)-bongkrekic acid, a potent apoptosis inhibitor, has been accomplished by employing a convergent strategy based on the Suzuki-Miyaura coupling of three fully functionalized segments.
引用
收藏
页码:2893 / 2904
页数:12
相关论文
共 50 条
  • [1] Synthesis of biphenylamines via Suzuki-Miyaura cross-coupling reactions
    Maj, Anna M.
    Delaude, Lionel
    Demonceau, Albert
    Noels, Alfred F.
    TETRAHEDRON, 2007, 63 (12) : 2657 - 2663
  • [2] Suzuki-Miyaura Coupling Reactions of Fluorohalobenzenes
    Iqbal, Shoaib
    Sharif, Muhammad
    Langer, Peter
    SYNLETT, 2021, 32 (18) : 1784 - 1795
  • [3] An expedient synthesis of ellipticine via Suzuki-Miyaura coupling
    Konakahara, Takeo
    Kiran, Y. B.
    Okuno, Yuri
    Ikeda, Reiko
    Sakai, Norio
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2335 - 2338
  • [4] Suzuki-Miyaura Coupling Reactions Using Phosphite Ligands
    Jang, Mihee
    Jo, Youngshin
    Oh, Il-Kwon
    Jung, Hyun Min
    Lee, Sunwoo
    SYNTHESIS-STUTTGART, 2009, (12): : 2073 - 2075
  • [5] Palladium catalysed sequential imine arylation/Suzuki-Miyaura coupling: synthesis of α-(biarylyl)benzylamines
    Marques, Carolina S.
    Locati, Abel
    Prates Ramalho, J. P.
    Burke, Anthony J.
    TETRAHEDRON, 2015, 71 (21) : 3314 - 3324
  • [6] Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki-Miyaura Cross-Coupling Reactions
    Fang, Yewen
    Zhang, Li
    Li, Jinjian
    Jin, Xiaoping
    Yuan, Meijuan
    Li, Ruifeng
    Wu, Rong
    Fang, Jianghua
    ORGANIC LETTERS, 2015, 17 (04) : 798 - 801
  • [7] Site Selective Synthesis of Pentaarylpyridines via Multiple Suzuki-Miyaura Cross-Coupling Reactions
    Reimann, Sebastian
    Ehlers, Peter
    Petrosyan, Andranik
    Kohse, Stefanie
    Spannenberg, Anke
    Surkus, Annette E.
    Ghochikyan, Tariel V.
    Saghyan, Ashot S.
    Lochbrunner, Stefan
    Kuehn, Oliver
    Ludwig, Ralf
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 1987 - 2008
  • [8] Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki-Miyaura Coupling Reactions
    Nishihara, Yasushi
    Okada, Yoshiaki
    Jiao, Jiao
    Suetsugu, Masato
    Lan, Ming-Tzu
    Kinoshita, Megumi
    Iwasaki, Masayuki
    Takagi, Kentaro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8660 - 8664
  • [9] The Suzuki-Miyaura Coupling of Nitroarenes
    Yadav, M. Ramu
    Nagaoka, Masahiro
    Kashihara, Myuto
    Zhong, Rong-Lin
    Miyazaki, Takanori
    Sakaki, Shigeyoshi
    Nakao, Yoshiaki
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (28) : 9423 - 9426
  • [10] Chemoselective Synthesis of Arylpyridines through Suzuki-Miyaura Cross-Coupling Reactions
    Perdomo Rivera, Rodisnel
    Ehlers, Peter
    Ohlendorf, Lars
    Torres Rodriguez, Eugenio
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (08) : 990 - 1003