Visible-Light-Promoted α-Benzylation of N-Phenyl α-Amino Acids to α-Amino Phenylpropanoids

被引:6
作者
Wang, Lin [1 ,2 ]
Li, Kang [1 ,2 ]
Ye, Tian [1 ,3 ]
Huang, Lei [1 ,3 ]
Wu, Huilan [1 ,2 ]
Zhang, Jingxuan [1 ,2 ]
Xie, Hongqi [1 ,3 ]
Liu, Yisong [1 ,3 ]
Zeng, Jianguo [1 ,3 ]
Cheng, Pi [1 ,3 ]
机构
[1] Hunan Agr Univ, Hunan Key Lab Tradit Chinese Vet Med, Changsha 410128, Hunan, Peoples R China
[2] Hunan Agr Univ, Coll Hort, Changsha 410128, Hunan, Peoples R China
[3] Hunan Agr Univ, Coll Vet Med, Changsha 410128, Hunan, Peoples R China
关键词
STREPTOMYCES SP TU-6075; PROTEASOME INHIBITORS; PHOTOREDOX CATALYSIS; ARYLOMYCIN-B; AMINO-ACIDS; SANGUINARINE; DERIVATIVES; HYPOCRELLIN; DOPA; CHELERYTHRINE;
D O I
10.1021/acs.joc.3c01196
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of & alpha;-amino phenylpropanoidsunder blue light-emitting diode irradiation has been developed through & alpha;-C-H benzylation of readily available N-phenylglycine ester with benzyl oxalates as a coupling partner under mildconditions. A range of N-phenyl glycine esters weresuccessfully converted to & alpha;-amino phenylpropanoid products inmoderate to good yields. The utility of this methodology is underlinedby its application to the late-state modification of natural products.
引用
收藏
页码:11924 / 11934
页数:11
相关论文
共 57 条
  • [1] Sanguinarine blocks cytokinesis in bacteria by inhibiting FtsZ assembly and bundling
    Beuria, TK
    Santra, MK
    Panda, D
    [J]. BIOCHEMISTRY, 2005, 44 (50) : 16584 - 16593
  • [2] Total synthesis of an atropdiastereomer of RP-66453 and determination of its absolute configuration
    Bois-Choussy, M
    Cristau, P
    Zhu, JP
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) : 4238 - 4241
  • [3] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids
    Cardillo, G
    Tomasini, C
    [J]. CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) : 117 - &
  • [4] Phosphotyrosine isosteres: past, present and future
    Cerullia, Robert A.
    Kritzer, Joshua A.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (04) : 583 - 605
  • [5] Exploring the Formation and Recognition of an Important G-Quadruplex in a HIF1α Promoter and Its Transcriptional Inhibition by a Benzo[c]phenanthridine Derivative
    Chen, Han
    Long, Haitao
    Cui, Xiaojie
    Zhou, Jiang
    Xu, Ming
    Yuan, Gu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (06) : 2583 - 2591
  • [6] Synthesis of 5-methyl phenanthridium derivatives: A new class of human DOPA decarboxylase inhibitors
    Cheng, Pi
    Zhou, Jie
    Qing, Zhixing
    Kang, Weisong
    Liu, Sheng
    Liu, Wei
    Xie, Hongqi
    Zeng, Jianguo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (12) : 2712 - 2716
  • [7] Dihydrosanguinarine Enhances Glucose Uptake in Mouse 3T3-L1 Cells
    Chow, Yit-Lai
    Iwata, Yuko
    Sato, Fumihiko
    [J]. ACS OMEGA, 2017, 2 (10): : 6916 - 6925
  • [8] ROLES OF OXYGEN AND PHOTOINDUCED ACIDIFICATION IN THE LIGHT-DEPENDENT ANTIVIRAL ACTIVITY OF HYPOCRELLIN-A
    FEHR, MJ
    CARPENTER, SL
    WANNEMUEHLER, Y
    PETRICH, JW
    [J]. BIOCHEMISTRY, 1995, 34 (48) : 15845 - 15848
  • [9] Photochemistry and photophysics of coordination compounds: Iridium
    Flamigni, Lucia
    Barbieri, Andrea
    Sabatini, Cristiana
    Ventura, Barbara
    Barigelletti, Francesco
    [J]. PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 : 143 - 203
  • [10] Deoxygenative Borylation of Secondary and Tertiary Alcohols
    Friese, Florian W.
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (28) : 9561 - 9564