Microwave-mediated synthesis of a cyclic heptapeptoid through consecutive Ugi reactions

被引：9
作者：
Barreto, Angelica de Fatima S. [1 ]
Andrade, Carlos Kleber Z. [1 ]
机构：
[1] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet, BR-70910970 Brasilia, DF, Brazil
来源：
TETRAHEDRON | 2018年 / 74卷 / 48期
关键词：
Cyclic peptoids; Consecutive Ugi reactions; Isocyanide-based multicomponent reactions (IMCRs); Microwave-mediated reactions; Macroheterocycles; MULTICOMPONENT REACTIONS; NATURAL-PRODUCTS; PEPTOIDS; SOLVENT; PEPTIDE; CHEMISTRY;
D O I：
10.1016/j.tet.2018.10.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The combination of consecutive Isocyanide-based Multicomponent Reactions (IMCRs) allowed the synthesis of a cyclic heptapeptoid in a reduced number of steps. Herein, we describe this efficient approach using four consecutive Ugi reactions, being three Ugi four-center, four-component reactions, and one Ugi four-center, three-component reaction. Our strategy involved eight steps of which seven in a row were microwave-assisted with reaction times of 3-5 min and yields ranging from 88 to 98%. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6861 / 6865
页数：5
相关论文
共 41 条
  • [1] Carteritins A and B, cyclic heptapeptides from the marine sponge Stylissa carteri
    Afifi, Ahmed H.
    El-Desoky, Ahmed H.
    Kato, Hikaru
    Mangindaan, Remy E. P.
    de Voogd, Nicole J.
    Ammar, Nagwa M.
    Hifnawy, Mohammed S.
    Tsukamoto, Sachiko
    [J]. TETRAHEDRON LETTERS, 2016, 57 (11) : 1285 - 1288
  • [2] Microwave assisted solvent-, support- and catalyst-free synthesis of enaminones
    Andrade, Carlos Kleber Z.
    Barreto, Angelica de Fatima S.
    Silva, Wender A.
    [J]. ARKIVOC, 2008, : 226 - 232
  • [3] Euryjanicins E-G, poly-phenylalanine, and poly-proline cyclic heptapeptides from the Caribbean sponge Prosuberites laughlini
    Aviles, Edward
    Rodriguez, Abimael D.
    [J]. TETRAHEDRON, 2013, 69 (51) : 10797 - 10804
  • [4] The value of natural products to future pharmaceutical discovery
    Baker, Dwight D.
    Chu, Min
    Oza, Uma
    Rajgarhia, Vineet
    [J]. NATURAL PRODUCT REPORTS, 2007, 24 (06) : 1225 - 1244
  • [5] Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
    Barreto, Angelica de Fatima S.
    dos Santos, Veronica Alves
    Andrade, Carlos Kleber Z.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2596 - 2602
  • [6] Barreto ADS, 2017, CURR MICROWAV CHEM, V4, P168, DOI 10.2174/2213335604666170125123748
  • [7] Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions
    Barreto, Angelica de Fatima S.
    dos Santos, Veronica Alves
    Andrade, Carlos Kleber Z.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2865 - 2872
  • [8] Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids
    Barreto, Angelica de Fatima S.
    Vercillo, Otilie E.
    Wessjohann, Ludger A.
    Andrade, Carlos Kleber Z.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1017 - 1022
  • [9] Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions
    Barreto, Angelica de Fatima S.
    Vercillo, Otilie E.
    Birkett, Mike A.
    Caulfield, John C.
    Wessjohann, Ludger A.
    Andrade, Carlos Kleber Z.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5024 - 5027
  • [10] Barreto ADS, 2011, J BRAZIL CHEM SOC, V22, P462, DOI 10.1590/S0103-50532011000300008
12345