Total Synthesis of Thuggacin B

被引:31
作者
Bock, Martin
Dehn, Richard
Kirschning, Andreas [1 ]
机构
[1] Leibniz Univ Hannover, Inst Chim Organ, D-30167 Hannover, Germany
关键词
aldol reaction; antibiotics; Sonogashira reaction; total synthesis; tuberculosis;
D O I
10.1002/anie.200803271
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Final proof of the complete structures of thuggacins A-C was gained by a highly convergent and flexible total synthesis. Notable features include a substrate-controlled, titanium-mediated aldol reaction, a cross-metathesis approach for converting terminal alkenes into the corresponding vinyl iodides, and the cross-coupling of a complex vinyl iodide and terminal alkyne in the Sonogashira reaction. (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9134 / 9137
页数:4
相关论文
共 32 条
  • [1] REAKTIONEN MIT PHOSPHINALKYLENEN .12. EINE NEUE SYNTHESE VON ALLEN-CARBONSAUREESTERN
    BESTMANN, HJ
    HARTUNG, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (04): : 1198 - &
  • [2] Bock M., 2008, ANGEW CHEM, V120, P2341
  • [3] Stereochemical determination of thuggacins A-C, highly active antibiotics from the myxobacterium Sorangium cellulosum
    Bock, Martin
    Buntin, Kathrin
    Mueller, Rolf
    Kirschning, Andreas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2308 - 2311
  • [4] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES
    CHEN, KM
    HARDTMANN, GE
    PRASAD, K
    REPIC, O
    SHAPIRO, MJ
    [J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158
  • [5] Synthesis of bicyclo[3.1.0]hexanes functionalized at the tip of the cyclopropane ring. Application to the synthesis of carbocyclic nucleosides
    Comin, MJ
    Parrish, DA
    Deschamps, JR
    Marquez, VE
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 705 - 708
  • [6] The growing burden of tuberculosis - Global trends and interactions with the HIV epidemic
    Corbett, EL
    Watt, CJ
    Walker, N
    Maher, D
    Williams, BG
    Raviglione, MC
    Dye, C
    [J]. ARCHIVES OF INTERNAL MEDICINE, 2003, 163 (09) : 1009 - 1021
  • [7] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES
    EVANS, DA
    BARTROLI, J
    SHIH, TL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) : 2127 - 2129
  • [8] NICKEL PEROXIDE DEHYDROGENATION OF OXYGEN-CONTAINING, SULFUR-CONTAINING, AND NITROGEN-CONTAINING HETEROCYCLES
    EVANS, DL
    MINSTER, DK
    JORDIS, U
    HECHT, SM
    MAZZU, AL
    MEYERS, AI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (04) : 497 - 501
  • [9] Highly stereoselective aldol reactions of titanium enolates from ethyl alpha-silyloxyalkyl ketones
    Figueras, S
    Martin, R
    Romea, P
    Urpi, F
    Vilarrasa, J
    [J]. TETRAHEDRON LETTERS, 1997, 38 (09) : 1637 - 1640
  • [10] The thuggacins, novel antibacterial macrolides from Sorangium cellulosum acting against selected gram-positive bacteria
    Irschik, Herbert
    Reichenbach, Hans
    Hoefle, Gerhard
    Jansen, Rolf
    [J]. JOURNAL OF ANTIBIOTICS, 2007, 60 (12) : 733 - 738