Late-Stage Functionalization: Total Synthesis of Beauveamide A and Its Congeners and Their Anticancer Activities

被引:5
|
作者
Saha, Sanu [1 ]
Auddy, Sourya Shankar [1 ]
Chatterjee, Akash [2 ]
Sen, Prosenjit [2 ]
Goswami, Rajib Kumar [1 ]
机构
[1] Indian Assoc Cultivat Sci, Sch Chem Sci, Kolkata 700032, India
[2] Indian Assoc Cultivat Sci, Sch Biol Sci, Kolkata 700032, India
关键词
ESTERIFICATION; OCTALACTIN; ANHYDRIDE; LACTONE; REAGENT; DESIGN;
D O I
10.1021/acs.orglett.2c02699
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric total synthesis of cyclotetradepsipep-tide beauveamide A has been achieved for the first time. A macrolactamization strategy involving two possible sites has been explored to find the most effective route for cyclization. A late-stage functionalization approach has been adopted for easy access of non-natural analogues of beauveamide A for further biological evaluation. Interestingly, the anticancer activity of one of the synthesized analogues was better than that of the parent natural product.
引用
收藏
页码:7113 / 7117
页数:5
相关论文
共 50 条
  • [1] Enantioselective total synthesis of lycoposerramine congeners through late-stage nitrogen deletion
    Kenta Yokoi
    Hans Renata
    Nature Communications, 16 (1)
  • [2] Late-Stage Functionalization
    Boergel, Jonas
    Ritter, Tobias
    CHEM, 2020, 6 (08): : 1877 - 1887
  • [3] Total Synthesis of (−)-5-Deoxyenterocin and Attempted Late-Stage Functionalization Reactions
    Koser, Lilla
    Bach, Thorsten
    Chemistry - A European Journal, 2023, 29 (57):
  • [4] Total Synthesis of (-)-5-Deoxyenterocin and Attempted Late-Stage Functionalization Reactions
    Koser, Lilla
    Bach, Thorsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (57)
  • [5] Total Synthesis of (-)-Magnoshinin and (+)-Merrilliaquinone: Application of a Late-Stage Oxidative Functionalization Protocol
    Salam, Abdus
    Kumar, Dileep
    Sahu, Tonish Kumar
    Khan, Rahimuddin
    Khan, Tabrez
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (18)
  • [6] Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization
    Konrad, David B.
    Frank, James A.
    Trauner, Dirk
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (13) : 4364 - 4368
  • [7] Electrochemical Late-Stage Functionalization
    Wang, Yulei
    Dana, Suman
    Long, Hao
    Xu, Yang
    Li, Yanjun
    Kaplaneris, Nikolaos
    Ackermann, Lutz
    CHEMICAL REVIEWS, 2023, 123 (19) : 11269 - 11335
  • [8] Bioinspired Synthesis of Allysine for Late-Stage Functionalization of Peptides
    Emenike, Benjamin
    Shahin, Sophia
    Raj, Monika
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (22)
  • [9] Visible-Light Photoredox Catalysis in the Late-Stage Functionalization of Anticancer Agents
    Singh, Praveen P.
    Srivastava, Vishal
    CHEMISTRYSELECT, 2023, 8 (44):
  • [10] Late-stage functionalization of 5-nitrofurans derivatives and their antibacterial activities
    Chen, Geshuyi
    Chang, Zhe
    Yuan, Pei
    Wang, Si
    Yang, Yongxiu
    Liang, Xiaolei
    Zhao, Depeng
    RSC ADVANCES, 2023, 13 (05) : 3204 - 3209