Catalytic Asymmetric Total Synthesis of Tangutorine

被引:25
|
作者
Nemoto, Tetsuhiro [1 ]
Yamamoto, Eri [1 ]
Franzen, Robert [1 ]
Fukuyama, Takashi [1 ]
Wu, Riliga [1 ]
Fukamachi, Toshihiko [1 ]
Kobayashi, Hiroshi [1 ]
Hamada, Yasumasa [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
CHIROGENIC DIAMINOPHOSPHINE OXIDES; STEREOSELECTIVE TOTAL-SYNTHESIS; ALLYLIC SUBSTITUTION; PALLADIUM; DIAPHOXS; ACID; (+/-)-TANGUTORINE; NUCLEOPHILES; DERIVATIVES; CYCLIZATION;
D O I
10.1021/ol902929a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantioselective total synthesis of tangutorine has been achieved, wherein a Pd-catalyzed asymmetric allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand was the key step.
引用
收藏
页码:872 / 875
页数:4
相关论文
共 50 条
  • [1] First total synthesis of (±)-tangutorine
    Putkonen, T
    Tolvanen, A
    Jokela, R
    TETRAHEDRON LETTERS, 2001, 42 (37) : 6593 - 6594
  • [2] Total synthesis of the monoterpenoid alkaloid (±)-tangutorine
    van den Broek, Sebastiaan A. M. W.
    Lemmers, Jaap G. H.
    van Delft, Floris L.
    Rutjes, Floris P. J. T.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (05) : 945 - 951
  • [3] Microwave-assisted total synthesis of tangutorine
    Flink, Heli
    Jokela, Reija
    TETRAHEDRON, 2012, 68 (20) : 3811 - 3814
  • [4] Catalytic asymmetric total synthesis of (+)-yohimbine
    Mergott, Dustin J.
    Zuend, Stephan J.
    Jacobsen, Eric N.
    ORGANIC LETTERS, 2008, 10 (05) : 745 - 748
  • [5] Catalytic, Asymmetric Total Synthesis of (+)-?-, (+)-?-, (+)-?-, and(-)-?-Lycorane
    Zhang, Tian-Yuan
    Zhang, Lu-Yue
    Liang, Xiao
    Wei, Kun
    Yang, Yu-Rong
    ORGANIC LETTERS, 2022, 24 (15) : 2905 - 2909
  • [6] Catalytic Asymmetric Total Synthesis of (+)-Caprazol
    Gopinath, Purushothaman
    Wang, Lu
    Abe, Hikaru
    Ravi, Gandamala
    Masuda, Takashi
    Watanabe, Takumi
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2014, 16 (12) : 3364 - 3367
  • [7] A catalytic asymmetric total synthesis of (-)-perophoramidine
    Trost, B. M.
    Osipov, M.
    Krueger, S.
    Zhang, Y.
    CHEMICAL SCIENCE, 2015, 6 (01) : 349 - 353
  • [8] The catalytic asymmetric total synthesis of elatol
    White, David E.
    Stewart, Ian C.
    Grubbs, Robert H.
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) : 810 - +
  • [9] Catalytic Asymmetric Total Synthesis of Leucinostatin A
    Watanabe, Takumi
    Abe, Hikaru
    Shibasaki, Masakatsu
    CHEMICAL RECORD, 2021, 21 (01): : 175 - 187
  • [10] Catalytic Asymmetric Total Synthesis of Exiguolide
    Oka, Kengo
    Fuchi, Shunsuke
    Komine, Keita
    Fukuda, Hayato
    Hatakeyama, Susumi
    Ishihara, Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (56) : 12862 - 12867