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
  • [41] Current Applications of Suzuki-Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update
    Koshvandi, Afsaneh Taheri Kal
    Heravi, Majid M.
    Momeni, Tayebeh
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (03)
  • [42] Total Synthesis of Hydroxy-α- and Hydroxy-β-sanshool Using Suzuki-Miyaura Coupling
    Igarashi, Yasushi
    Aoki, Katsuyuki
    Nishimura, Hiroaki
    Morishita, Isao
    Usui, Kimitoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (08) : 1088 - 1091
  • [43] Total synthesis of aristolactams via a one-pot suzuki-miyaura coupling/aldol condensation cascade reaction
    Kim, Joa Kyum
    Kim, Young Ha
    Nam, Ho Tae
    Kim, Bum Tae
    Heo, Jung-Nyoung
    ORGANIC LETTERS, 2008, 10 (16) : 3543 - 3546
  • [44] Synthesis of Phenyl- and Pyridyl-substituted Benzyloxybenzaldehydes Suzuki-miyaura Coupling Reactions
    Bolcskei, Hedvig
    Nemet-Hanzelik, Andrea
    Dubrovay, Zsofia
    Hada, Viktor
    Keglevich, Gyorgy
    LETTERS IN DRUG DESIGN & DISCOVERY, 2019, 16 (11) : 1248 - 1257
  • [45] Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki-Miyaura Coupling Reactions
    Benhamou, Laure
    Besnard, Celine
    Kuendig, E. Peter
    ORGANOMETALLICS, 2014, 33 (01) : 260 - 266
  • [46] Green synthesis of a palladium-polyaniline nanocomposite for green Suzuki-Miyaura coupling reactions
    Dutt, Sunil
    Kumar, Raj
    Siril, Prem Felix
    RSC ADVANCES, 2015, 5 (43): : 33786 - 33791
  • [47] Synthesis of enantiomerically enriched triarylmethanes by enantiospecific suzuki-miyaura cross-coupling reactions
    Crudden, C.M. (cruddenc@chem.queensu.ca), 1600, American Chemical Society (136):
  • [48] Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki-Miyaura Cross-Coupling Reactions
    Matthew, Smitha C.
    Glasspoole, Ben W.
    Eisenberger, Patrick
    Crudden, Cathleen M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (16) : 5828 - 5831
  • [49] Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions
    Yang, Xiaoyin
    Don, Xi
    Muellen, Klaus
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (04) : 759 - 766
  • [50] Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki-Miyaura coupling reactions
    Okten, Salih
    JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (7-8) : 274 - 280