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
  • [1] Advances in N-Heterocyclic Carbene Catalysis for Natural Product Synthesis
    Que, Yonglei
    He, Haibing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (37) : 5917 - 5925
  • [2] Enantioselective Total Synthesis of (-)-Δ9-Tetrahydrocannabinol via N-Heterocyclic Carbene Catalysis
    Ametovski, Adam
    Lupton, David W.
    ORGANIC LETTERS, 2019, 21 (04) : 1212 - 1215
  • [3] Enantioselective Synthesis of δ-Carbolinones via N-Heterocyclic Carbene Catalysis
    Zhang, Simiao
    Lin, Chen
    Liu, Chaolei
    Du, Ding
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10441 - 10448
  • [4] Divergent Synthesis of Dihydropyranone Stereoisomers via N-Heterocyclic Carbene Catalysis
    Zhao, Changgui
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) : 1668 - 1672
  • [5] Synthesis of N-heterocyclic carbene boranes via silver N-heterocyclic carbene complexes
    Ono, Shintaro
    Watanabe, Takashi
    Nakamura, Yosuke
    Sato, Hiroyasu
    Hashimoto, Toru
    Yamaguchi, Yoshitaka
    POLYHEDRON, 2017, 137 : 296 - 305
  • [6] Radical N-heterocyclic carbene catalysis for β-ketocarbonyl synthesis
    Ishii, Takuya
    Nagao, Kazunori
    Ohmiya, Hirohisa
    TETRAHEDRON, 2021, 91
  • [7] Modular synthesis of α-aryl β-perfluoroalkyl ketones via N-heterocyclic carbene catalysis
    Yang, Hai-Bin
    Wang, Zhi-Hou
    Li, Jin-Mei
    Wu, Chuande
    CHEMICAL COMMUNICATIONS, 2020, 56 (26) : 3801 - 3804
  • [8] Oxidative N-Heterocyclic Carbene Catalysis
    De Risi, Carmela
    Brandolese, Arianna
    Di Carmine, Graziano
    Ragno, Daniele
    Massi, Alessandro
    Bortolini, Olga
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (04)
  • [9] Iminoacylation of Alkenes via Photoredox N-Heterocyclic Carbene Catalysis
    Dong, Yi-Xiong
    Zhang, Chun-Lin
    Gao, Zhong-Hua
    Ye, Song
    ORGANIC LETTERS, 2023, : 855 - 860
  • [10] N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium
    Zhang, Changhe
    Hooper, Joel F.
    Lupton, David W.
    ACS CATALYSIS, 2017, 7 (04): : 2583 - 2596
12345