Xanthone Natural Products via N-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin

被引：26
|
作者：
Suzuki, Yumiko [1 ]
Fukuta, Yoshinori [1 ]
Ota, Shinya [1 ]
Kamiya, Masayo [1 ]
Sato, Masayuki [1 ]
机构：
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 10期
关键词：
NUCLEOPHILIC AROYLATION; ACIDIC SPHINGOMYELINASE; IMIDAZOLIDENYL CARBENE; GARCINIA-HANBURYI; ORGANOCATALYSTS; FRUITS; ETHERS;
D O I：
10.1021/jo200303c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of atroviridin has been accomplished by a linear route involving the N-heterocyclic carbene (NHC)-catalyzed aroylation of the fluorobenzene derivative, Claisen cyclization of the O-propargylated benzo-phenones, and intramolecular 1,4-addition of the quinone intermediates. The result provides a viable route to xanthone natural products.
引用
收藏
页码：3960 / 3967
页数：8
相关论文
共 50 条
  • [41] Iron N-heterocyclic carbene complexes in homogeneous catalysis
    Liang, Qiuming
    Song, Datong
    CHEMICAL SOCIETY REVIEWS, 2020, 49 (04) : 1209 - 1232
  • [42] Water in N-Heterocyclic Carbene-Assisted Catalysis
    Levin, Efrat
    Ivry, Elisa
    Diesendruck, Charles E.
    Lemcoff, N. Gabriel
    CHEMICAL REVIEWS, 2015, 115 (11) : 4607 - 4692
  • [43] N-Heterocyclic Carbene (NHC)/Metal Cooperative Catalysis
    Kazunori Nagao
    Hirohisa Ohmiya
    Topics in Current Chemistry, 2019, 377
  • [44] A cooperative N-heterocyclic carbene/palladium catalysis system
    Liu, Kun
    Hovey, M. Todd
    Scheidt, Karl A.
    CHEMICAL SCIENCE, 2014, 5 (10) : 4026 - 4031
  • [45] N-Heterocyclic Carbene Catalysis under Oxidizing Conditions
    Dzieszkowski, Krzysztof
    Rafinski, Zbigniew
    CATALYSTS, 2018, 8 (11)
  • [46] N-Heterocyclic Carbene (NHC)/Metal Cooperative Catalysis
    Nagao, Kazunori
    Ohmiya, Hirohisa
    TOPICS IN CURRENT CHEMISTRY, 2019, 377 (06)
  • [47] N-heterocyclic carbene ligands in asymmetric synthesis: Total synthesis of baconipyrone C
    Gillingham, Dennis G.
    Hoveyda, Amir H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [48] β-Sulfonylation of α-bromoenals enabled by N-heterocyclic carbene catalysis
    Jin, Shiyi
    Fang, Shuaishuai
    Ma, Rui
    Liang, Zheng
    Xu, Ye
    Lu, Tao
    Du, Ding
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (19): : 3392 - 3396
  • [49] Discovering New Reactions with N-Heterocyclic Carbene Catalysis
    Phillips, Eric M.
    Chan, Audrey
    Scheidt, Karl A.
    ALDRICHIMICA ACTA, 2009, 42 (03) : 55 - 66
  • [50] Cooperative Lewis acid/N-heterocyclic carbene catalysis
    Cohen, Daniel T.
    Scheidt, Karl A.
    CHEMICAL SCIENCE, 2012, 3 (01) : 53 - 57
12345