A Modular Approach to the Total Synthesis of Tunicamycins

被引：69
|
作者：
Li, Jiakun [1 ]
Yu, Biao [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 22期
基金：
中国国家自然科学基金;
关键词：
glycosylation; gold; nucleosides; total synthesis; tunicamycin; GLYCOSYL ORTHO-ALKYNYLBENZOATES; HIGHLY STEREOSELECTIVE-SYNTHESIS; ANTIBIOTIC TUNICAMYCINS; BIOLOGICAL-ACTIVITY; STRUCTURAL ELUCIDATION; ANTIVIRAL ACTIVITY; N-GLYCOSYLATION; HERBICIDIN C; STREPTOVIRUDINS; BIOSYNTHESIS;
D O I：
10.1002/anie.201501890
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the Nglycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and Nglycosylation, and final Nacylation were used as the key steps.
引用
收藏
页码：6618 / 6621
页数：4
相关论文
共 50 条
  • [1] SYNTHETIC APPROACH TOWARD ANTIBIOTIC TUNICAMYCINS .6. TOTAL SYNTHESIS OF TUNICAMYCINS
    SUAMI, T
    SASAI, H
    MATSUNO, K
    SUZUKI, N
    FUKUDA, Y
    SAKANAKA, O
    [J]. TETRAHEDRON LETTERS, 1984, 25 (40) : 4533 - 4536
  • [2] Modular approach to the total synthesis of the lamellarins.
    Handy, ST
    Zhang, YN
    Bregman, H
    Zhang, WL
    Kudgus, R
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U248 - U248
  • [3] A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids
    Tian, Guang
    Zhang, Yi-Chi
    Qin, Chuanguang
    Wang, Jie
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 10 (01) : 68 - 73
  • [4] A Mild and Modular Approach to the Total Synthesis of Desferrioxamine B
    Markham, Todd E.
    Codd, Rachel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 5118 - 5125
  • [5] SYNTHETIC APPROACHES TOWARD ANTIBIOTIC TUNICAMYCINS .8. TOTAL SYNTHESIS OF TUNICAMYCIN
    SUAMI, T
    SASAI, H
    MATSUNO, K
    SUZUKI, N
    [J]. CARBOHYDRATE RESEARCH, 1985, 143 (NOV) : 85 - 96
  • [6] SYNTHETIC APPROACH TOWARD ANTIBIOTIC TUNICAMYCINS
    FUKUDA, Y
    SASAI, H
    SUAMI, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (06) : 1830 - 1834
  • [7] Modular total synthesis approach towards salvinorin A inspired designer opioids
    Sherwood, Alexander
    Williamson, Samuel
    Saylor, Rachel
    Prisinzano, Thomas
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [8] A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C
    Raguz, Luka
    Peng, Chia-Chi
    Kaiser, Marcel
    Gorls, Helmar
    Beemelmanns, Christine
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (05)
  • [9] The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular "Inside-Out" Approach
    Scharnagel, Dagmar
    Goller, Jessica
    Deibl, Nicklas
    Milius, Wolfgang
    Breuning, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2432 - 2435
  • [10] Modular approach to Annonaceous acetogenins. Total synthesis of asimicin and bullatacin.
    Sinha, SC
    SinhaBagchi, A
    Yazbak, A
    Keinan, E
    [J]. TETRAHEDRON LETTERS, 1995, 36 (51) : 9257 - 9260
12345