Approach to pactamycin analogues using rhodium(II)-catalyzed alkene aziridination and C(sp3)-H amination reactions

被引：8
作者：
Rodrigues, Romain [1 ]
Lazib, Yanis [1 ]
Maury, Julien [1 ,2 ]
Neuville, Luc [1 ]
Leboeuf, David [2 ]
Dauban, Philippe [1 ]
Darses, Benjamin [1 ]
机构：
[1] Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS,UPR 2301, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Univ Paris Saclay, Univ Paris Sud, Inst Chim Mol & Mat Orsay, CNRS,UMR 8182, Batiment 420, F-91405 Orsay, France
来源：
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 06期
关键词：
C-H AMINATION; COPPER-CATALYZED AZIRIDINATION; 30S RIBOSOMAL-SUBUNIT; HIGHLY EFFICIENT; CORE FRAMEWORK; ANTITUMOR; BONDS; CYCLOPENTANE; CONSTRUCTION; ANTIBIOTICS;
D O I：
10.1039/c7qo00878c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dirhodium(ii)-catalyzed nitrene transfers have been used to prepare a novel synthetic platform bearing the triamino moiety present in pactamycin, jogyamycin and cranomycin. Catalytic intramolecular C(sp(3))-H amination and alkene aziridination reactions, the latter followed by a nucleophilic aziridine ring opening, are the key steps of this strategy.
引用
收藏
页码：948 / 953
页数：6
相关论文
共 72 条
  • [1] Interrogating the Tailoring Steps of Pactamycin Biosynthesis and Accessing New Pactamycin Analogues
    Abugrain, Mostafa E.
    Lu, Wanli
    Li, Yuexin
    Serrill, Jeffrey D.
    Brumsted, Corey J.
    Osborn, Andrew R.
    Alani, Adam
    Ishmael, Jane E.
    Kelly, Jane X.
    Mahmud, Taifo
    [J]. CHEMBIOCHEM, 2016, 17 (17) : 1585 - 1588
  • [2] DIRECTED BIOSYNTHESIS OF 5''-FLUOROPACTAMYCIN IN STREPTOMYCES-PACTUM
    ADAMS, ES
    RINEHART, KL
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (12) : 1456 - 1465
  • [3] A ROUTE TO FUNCTIONALIZED BRANCHED-CHAIN AMINO-SUGARS VIA NITROUS-ACID PROMOTED SPIROAZIRIDINE FORMATION
    ALVES, RJ
    CASTILLON, S
    DESSINGES, A
    HERCZEGH, P
    LOPEZ, JC
    LUKACS, G
    OLESKER, A
    THANG, TT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4616 - 4618
  • [4] Argoudelis A.D., 1962, ANTIMICROB AGENTS CH, P191
  • [5] Analyzing Site Selectivity in Rh2(esp)2-Catalyzed Intermolecular C-H Amination Reactions
    Bess, Elizabeth N.
    DeLuca, Ryan J.
    Tindall, Daniel J.
    Oderinde, Martins S.
    Roizen, Jennifer L.
    Du Bois, J.
    Sigman, Matthew S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) : 5783 - 5789
  • [6] Bhuyan B.K., 1962, Antimicrob. Agents Chemother, P184
  • [7] PACTAMYCIN AN ANTIBIOTIC THAT INHIBITS PROTEIN SYNTHESIS
    BHUYAN, BK
    [J]. BIOCHEMICAL PHARMACOLOGY, 1967, 16 (08) : 1411 - &
  • [8] The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit
    Brodersen, DE
    Clemons, WM
    Carter, AP
    Morgan-Warren, RJ
    Wimberly, BT
    Ramakrishnan, V
    [J]. CELL, 2000, 103 (07) : 1143 - 1154
  • [9] Buendia J., 2016, ANGEW CHEM, V128, P7656, DOI DOI 10.1002/ANGE.201602022
  • [10] Dirhodium(II)-Catalyzed C(sp3)-H Amination Using Iodine(III) Oxidants
    Buendia, Julien
    Grelier, Gwendal
    Dauban, Philippe
    [J]. ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 64, 2015, 64 : 77 - 118
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