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
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共 72 条
  • [11] Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes
    Chang, Joyce Wei Wei
    Ton, Thi My Uyen
    Chan, Philip Wai Hong
    [J]. CHEMICAL RECORD, 2011, 11 (06) : 331 - 357
  • [12] Practical copper(I)-catalysed amidation of aldehydes
    Chang, Joyce Wei Wei
    Ton, Thi My Uyen
    Tania, Stefani
    Taylor, Paul C.
    Chan, Philip Wai Hong
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (06) : 922 - 924
  • [13] Rhodium-catalyzed enantioselective desymmetrization of meso-3,5-dimethyl glutaric anhydride:: A general strategy to syn-deoxypolypropionate synthons
    Cook, Matthew J.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (30) : 9302 - +
  • [14] Transition metal-catalyzed iodine(III)-mediated nitrene transfer reactions: efficient tools for challenging syntheses
    Darses, B.
    Rodrigues, R.
    Neuville, L.
    Mazurais, M.
    Dauban, P.
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (03) : 493 - 508
  • [15] Coinage metal catalyzed C-H bond functionalization of hydrocarbons
    Diaz-Requejo, M. Mar
    Perez, Pedro J.
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3379 - 3394
  • [16] Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: The universally conserved residues G693 and C795 regulate P-site RNA binding
    Dinos, G
    Wilson, DN
    Teraoka, Y
    Szaflarski, W
    Fucini, P
    Kalpaxis, D
    Nierhaus, KH
    [J]. MOLECULAR CELL, 2004, 13 (01) : 113 - 124
  • [17] 8''-HYDROXYPACTAMYCIN AND 7-DEOXYPACTAMYCIN, NEW MEMBERS OF THE PACTAMYCIN GROUP
    DOBASHI, K
    ISSHIKI, K
    SAWA, T
    OBATA, T
    HAMADA, M
    NAGANAWA, H
    TAKITA, T
    TAKEUCHI, T
    UMEZAWA, H
    BEI, HS
    ZHU, BQ
    TONG, C
    XU, WS
    [J]. JOURNAL OF ANTIBIOTICS, 1986, 39 (12) : 1779 - 1783
  • [18] Catalyst-Controlled and Tunable, Chemoselective Silver-Catalyzed Intermolecular Nitrene Transfer: Experimental and Computational Studies
    Dolan, Nicholas S.
    Scamp, Ryan J.
    Yang, Tzuhsiung
    Berry, John F.
    Schomaker, Jennifer M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (44) : 14658 - 14667
  • [19] Recent advances in transition metal-catalyzed N-atom transfer reactions of azides
    Driver, Tom G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) : 3831 - 3846
  • [20] Intramolecular PhI=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
    Duran, F
    Leman, L
    Ghini, A
    Burton, G
    Dauban, P
    Dodd, RH
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2481 - 2483
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