Total synthesis of aristolactams via a one-pot suzuki-miyaura coupling/aldol condensation cascade reaction

被引:74
|
作者
Kim, Joa Kyum [1 ]
Kim, Young Ha [1 ]
Nam, Ho Tae [1 ]
Kim, Bum Tae [1 ]
Heo, Jung-Nyoung [1 ]
机构
[1] Korea Res Inst Chem Technol, Ctr Med Chem, Taejon 305600, South Korea
关键词
D O I
10.1021/ol801291k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki-Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formyl phenyl boronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam.
引用
收藏
页码:3543 / 3546
页数:4
相关论文
共 50 条
  • [21] Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction
    Hsu, Shao-Chien
    Narsingam, Mogili
    Lin, Yi-Fang
    Hsu, Feng-Lin
    Uang, Biing-Jiun
    TETRAHEDRON, 2013, 69 (12) : 2572 - 2576
  • [22] Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine
    Lim, Hye Sun
    Choi, Young Lok
    Heo, Jung-Nyoung
    ORGANIC LETTERS, 2013, 15 (18) : 4718 - 4721
  • [23] High-quality conjugated polymers via one-pot Suzuki-Miyaura homopolymerization
    Zhou, Difei
    Doumon, Nutifafa Y.
    Abdu-Aguye, Mustapha
    Bartesaghi, Davide
    Loi, Maria A.
    Koster, L. Jan Anton
    Chiechi, Ryan C.
    Hummelen, Jan C.
    RSC ADVANCES, 2017, 7 (44) : 27762 - 27769
  • [24] Total synthesis of (-)-amathaspiramide A via a one-pot aldol addition/transamidification reaction
    Wang, Jun-Jie
    Bai, Rui-Xue
    Yang, Mao-Qi
    Chen, Zheng-Yu
    Wang, Min-Dan
    Zhao, Qian
    Lin, Guo-Qiang
    Fu, Jian-Guo
    Feng, Chen-Guo
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11) : 3045 - 3049
  • [25] Total Synthesis of (-)-Polycavernoside A: Suzuki-Miyaura Coupling Approach
    Kasai, Yusuke
    Ito, Takanori
    Sasaki, Makoto
    ORGANIC LETTERS, 2012, 14 (12) : 3186 - 3189
  • [26] One-pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C-H Oxidation/Aromatization
    Zhang, Yi
    Ding, Yuxin
    Chen, Rener
    Ma, Yongmin
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) : 5697 - 5707
  • [27] Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes
    Sato, Ko
    Tanaka, Hiroshi
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (36) : 9422 - 9428
  • [28] One-pot sequential four-component coupling via Cp*RuCl-catalyzed cyclotrimerization and Suzuki-Miyaura coupling
    Yamamoto, Y
    Ishii, J
    Nishiyama, H
    Itoh, K
    TETRAHEDRON, 2005, 61 (48) : 11501 - 11510
  • [29] One-pot Synthesis of Pd/Azo-polymer as an Efficient Catalyst for 4-Nitrophenol Reduction and Suzuki-Miyaura Coupling Reaction
    Yu, Yanlin
    Gong, Yuzhu
    Cao, Binbin
    Liu, Haidong
    Zhang, Xiaoli
    Han, Xu
    Lu, Shuanglong
    Cao, Xueqin
    Gu, Hongwei
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (07) : 837 - 844
  • [30] 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