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
  • [21] ALKYNYLBORANES IN THE SUZUKI-MIYAURA COUPLING
    SODERQUIST, JA
    MATOS, K
    RANE, A
    RAMOS, J
    TETRAHEDRON LETTERS, 1995, 36 (14) : 2401 - 2402
  • [22] ALKYNYLBORANES IN THE SUZUKI-MIYAURA COUPLING
    SODERQUIST, JA
    MATOS, K
    RANE, A
    RAMOS, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 293 - ORGN
  • [23] Aminative Suzuki-Miyaura coupling
    Onnuch, Polpum
    Ramagonolla, Kranthikumar
    Liu, Richard Y.
    SCIENCE, 2024, 383 (6686) : 1019 - 1024
  • [24] 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
  • [25] Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid
    Korenaga, T
    Kosaki, T
    Fukumura, R
    Ema, T
    Sakai, T
    ORGANIC LETTERS, 2005, 7 (22) : 4915 - 4917
  • [26] Acid Fluorides as Acyl Electrophiles in Suzuki-Miyaura Coupling
    Ogiwara, Yohei
    Sakino, Daisuke
    Sakurai, Yuka
    Sakai, Norio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (29) : 4324 - 4327
  • [27] Stereodivergent Synthesis of Arylcyclopropylamines by Sequential C-H Borylation and Suzuki-Miyaura Coupling
    Miyamura, Shin
    Araki, Misaho
    Suzuki, Takayoshi
    Yamaguchi, Junichiro
    Itami, Kenichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) : 846 - 851
  • [28] Synthesis of useful benzocyclobutene building blocks via the suzuki-miyaura coupling reaction
    Department of Chemistry, Indian Inst. of Technology-Bombay, Powai, Mumbai-400 076, India
    Synthesis, 2001, (13) : 1932 - 1934
  • [29] Application of Suzuki-Miyaura coupling reaction in the synthesis of salbutamol
    Chen, Liping
    Qiu, Zhongxuan
    Li, Zhenpeng
    Wang, Yuexing
    Huang, Longjiang
    Jingxi Huagong/Fine Chemicals, 2022, 39 (08): : 1716 - 1721
  • [30] Synthesis of 5,7-diarylindoles via Suzuki-Miyaura coupling in water
    Elumalai, Vijayaragavan
    Hansen, Jorn H.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (47) : 10343 - 10347