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
  • [31] Total Synthesis of Bongkrekic Acid via Sequential Suzuki-Miyaura Coupling Reactions
    Kanematsu, Makoto
    Shindo, Mitsuru
    Yoshida, Masahiro
    Shishido, Kozo
    SYNTHESIS-STUTTGART, 2009, (17): : 2893 - 2904
  • [32] Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction
    Chen, You
    Peng, Hui
    Pi, Yun-Xiao
    Meng, Tong
    Lian, Ze-Yu
    Yan, Meng-Qi
    Liu, Yan
    Liu, Sheng-Hua
    Yu, Guang-Ao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) : 3236 - 3242
  • [33] 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
  • [34] 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
  • [35] One-Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction
    Loureiro, Daniela R. P.
    Soares, Jose X.
    Maia, Ana
    Silva, Andre M. N.
    Rangel, Maria
    Azevedo, Carlos M. G.
    Hansen, Steffen, V
    Ulven, Trond
    Pinto, Madalena M. M.
    Reis, Salette
    Afonso, Carlos M. M.
    CHEMISTRYSELECT, 2021, 6 (18): : 4511 - 4514
  • [36] Synthesis of useful benzocyclobutene building blocks via the Suzuki-Miyaura coupling reaction
    Kotha, S
    Lahiri, K
    Sreenivasachary, N
    SYNTHESIS-STUTTGART, 2001, (13): : 1932 - 1934
  • [37] Synthesis of highly functionalised dibenzylglycine derivatives via the Suzuki-Miyaura coupling reaction
    Kotha, S
    Behera, M
    Kumar, RV
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (01) : 105 - 108
  • [38] Two-Step One-Pot Synthesis of Benzoannulated Spiroacetals by Suzuki-Miyaura Coupling/Acid-Catalyzed Spiroacetalization
    Butkevich, Alexey N.
    Corbu, Andrei
    Meerpoel, Lieven
    Stansfield, Ian
    Angibaud, Patrick
    Bonnet, Pascal
    Cossy, Janine
    ORGANIC LETTERS, 2012, 14 (19) : 4998 - 5001
  • [39] One-pot sequential synthesis of quinazolin-8-ol derivatives employing heterogeneous catalyst for Suzuki-Miyaura coupling
    Sharma, Vijay Kumar
    Barde, Anup
    Rattan, Sunita
    SYNTHETIC COMMUNICATIONS, 2020, 50 (19) : 2962 - 2968
  • [40] One-Pot Suzuki-Miyaura C-C Coupling Reaction versus Stepwise Reaction Involving Isolated Synthesized Catalyst Addition
    Koudehi, Masoumeh Foroutan
    Zibaseresht, Ramin
    JOURNAL OF CHEMICAL EDUCATION, 2020, 97 (10) : 3822 - 3828