Total Synthesis of (±)-Hippolachnin A

被引：84
作者：
Ruider, Stefan A. [1 ]
Sandmeier, Tobias [1 ]
Carreira, Erick M. [1 ]
机构：
[1] ETH, Lab Organ Chem, CH-8093 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 08期
关键词：
ene reaction; hippolachninA; natural products; photochemistry; total synthesis; CATALYZED HYDROHYDRAZINATION; MOLECULAR-OXYGEN; BCDE-RING; OLEFINS; ALKENES; HYDROAZIDATION; CYCLOADDITION; PHENYLSILANE; ACCESS; METAL;
D O I：
10.1002/anie.201410419
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first total synthesis of the marine polyketide (+/-)-hippolachninA has been achieved in nine linear steps and an overall yield of 9%. Rapid access to the oxacyclobutapentalene core structure was secured by strategic application of an ene cyclization.
引用
收藏
页码：2378 / 2382
页数：5
相关论文
共 69 条
  • [1] A rhodium-catalyzed C-H activation/cycloisomerization tandem
    Aissa, Christophe
    Fuerstner, Alois
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) : 14836 - +
  • [2] Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences
    Alcaide, B
    Almendros, P
    Rodríguez-Acebes, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) : 2346 - 2351
  • [3] [Anonymous], 2010, ANGEW CHEM
  • [4] [Anonymous], 2013, ANGEW CHEM INT ED
  • [5] [Anonymous], CHEM SCI
  • [6] [Anonymous], 2014, ANGEW CHEM
  • [7] Palladium-Catalyzed Allylic Substitution at Four-Membered-Ring Systems: Formation of η1-Allyl Complexes and Electrocyclic Ring Opening
    Audisio, Davide
    Gopakumar, Gopinadhanpillai
    Xie, Lan-Gui
    Alves, Luis G.
    Wirtz, Cornelia
    Martins, Ana M.
    Thiel, Walter
    Fares, Christophe
    Maulide, Nuno
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (24) : 6313 - 6316
  • [8] Bauer I., 2008, IRON CATALYSIS ORGAN
  • [9] A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (02) : 1372 - 1377
  • [10] Bis(imino)pyridine iron(II) alkyl cations for olefin polymerization
    Bouwkamp, MW
    Lobkovsky, E
    Chirik, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) : 9660 - 9661
1234567