Intermolecular oxidative enolate heterocoupling

被引:165
作者
Baran, Phil S. [1 ]
DeMartino, Michael P. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
C-C coupling; enolates; lignans; synthetic methods; total synthesis;
D O I
10.1002/anie.200603024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) No priming necessary: The intermolecular oxidative heterocoupling of imides and oxindoles to esters, ketones, and lactones is shown for the first time to be synthetically viable. Strategic use of the initial oxidation state of the reactants allows for the excision of prefunctionalization steps (halogenation, enol-silane formation) and allows for the concise synthesis of unsymmetrical lignans, such as (-)-bursehernin (1). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7083 / 7086
页数:4
相关论文
共 27 条
  • [1] [Anonymous], 2005, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200461864
  • [2] BALKOVEC JM, 2001, Patent No. 29687
  • [3] Enantioselective total synthesis of avrainvillamide and the stephacidins
    Baran, Phil S.
    Hafensteiner, Benjamin D.
    Ambhaikar, Narendra B.
    Guerrero, Carlos A.
    Gallagher, John D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) : 8678 - 8693
  • [4] Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B
    Baran, PS
    Guerrero, CA
    Hafensteiner, BD
    Ambhaikar, NB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) : 3892 - 3895
  • [5] Short, enantioselective total synthesis of Stephacidin A
    Baran, PS
    Guerrero, CA
    Ambhaikar, NB
    Hafensteiner, BD
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) : 606 - 609
  • [6] Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
    Baran, PS
    Richter, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) : 7450 - 7451
  • [7] BARAN PS, 2005, ANGEW CHEM, V117, P615
  • [8] BARAN PS, 2005, ANGEW CHEM, V117, P3960
  • [9] OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS - THE TOTAL SYNTHESIS OF (+/-)-HINOKININ AND (+/-)-FOMENTARIC ACID
    BELLETIRE, JL
    FRY, DF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) : 2549 - 2555
  • [10] OXIDATION BY METAL-SALTS .12. NOVEL ONE-STEP SYNTHESIS OF 1,4 DIKETONES
    DESSAU, RM
    HEIBA, EI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) : 3457 - 3459