A novel and highly stereoselective intramolecular formal [3+3] cycloaddition reaction of vinylogous amides tethered with α,β-unsaturated aldehydes:: A formal total synthesis of (+)-gephyrotoxin

被引：0
|
作者：
Wei, LL [1 ]
Hsung, RP [1 ]
Sklenicka, HM [1 ]
Gerasyuto, AI [1 ]
机构：
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2001年 / 40卷 / 08期
关键词：
D O I：
10.1002/1521-3773(20010417)40:8<1516::AID-ANIE1516>3.0.CO;2-V
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Complex piperidinyl heterocycles (for example, 2) were accessed by using a novel intramolecular formal [3+3] cycloaddition reaction of vinylogous amides tethered with enals (for example, 1). This method has been applied to a formal total sythesis of (+)-gephyrotoxin (3).
引用
收藏
页码：1516 / +
页数：4
相关论文
共 50 条
  • [21] Formal [3+3] cycloaddition strategy towards synthesis of highly functionalized piperidines.
    Sydorenko, N
    Hsung, R
    Hahn, JM
    Darwish, OS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U114 - U114
  • [22] Benzene construction via organocatalytic formal [3+3] cycloaddition reaction
    Zhu, Tingshun
    Zheng, Pengcheng
    Mou, Chengli
    Yang, Song
    Song, Bao-An
    Chi, Yonggui Robin
    NATURE COMMUNICATIONS, 2014, 5
  • [23] Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine
    Angle, SR
    El-Said, NA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) : 3608 - 3613
  • [24] Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine
    Angle, S.R., 1600, American Chemical Society (124):
  • [25] Benzene construction via organocatalytic formal [3+3] cycloaddition reaction
    Tingshun Zhu
    Pengcheng Zheng
    Chengli Mou
    Song Yang
    Bao-An Song
    Yonggui Robin Chi
    Nature Communications, 5
  • [26] Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes
    Chan, Audrey
    Scheidt, Karl A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) : 5334 - +
  • [27] Intramolecular formal aza-[3+3] cycloaddition approach for the synthesis of immunosuppressant FR901483.
    Sizova, EP
    Hsung, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U84 - U84
  • [28] A formal [3+3] cycloaddition approach to natural-product synthesis
    Hsung, RP
    Kurdyumov, AV
    Sydorenko, N
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (01) : 23 - 44
  • [29] Synthesis of azahexabenzocoronenium salts through a formal [3+3] cycloaddition strategy
    Zhang, Xinjiang
    Li, Donglin
    Tan, Cheryl Cai Hui
    Hanindita, Fiona
    Hamamoto, Yosuke
    Foster, Adam S.
    Kawai, Shigeki
    Ito, Shingo
    NATURE SYNTHESIS, 2024, 3 (10): : 1283 - 1291
  • [30] Intramolecular formal oxa-[3+3] cycloaddition approach to the ABD system of (±) phomactin A
    Tang, Yu
    Cole, Kevin P.
    Hsung, Richard P.
    Li, Gang
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
12345