Enantioselective Formal Total Syntheses of Didehydrostemofoline and Isodidehydrostemofoline through a Catalytic Dipolar Cycloaddition Cascade

被引:34
|
作者
Fang, Chao [1 ]
Shanahan, Charles S. [1 ]
Paull, Daniel H. [1 ]
Martin, Stephen F. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
基金
美国国家卫生研究院;
关键词
azomethine ylide; cascade reaction; dipolar cycloaddition; enantioselective synthesis; stemofoline alkaloids; total synthesis; STEMOFOLINE ALKALOIDS; STEMONA ALKALOIDS; ASPARAGAMINE-A; AZOMETHINE YLIDES; SEMISYNTHESIS; DERIVATIVES; RACEMOSUS; TOXICITY; ANALOGS;
D O I
10.1002/anie.201205274
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:10596 / 10599
页数:4
相关论文
共 50 条
  • [1] Asymmetric formal total synthesis of the stemofoline alkaloids: the evolution, development, and application of a catalytic dipolar cycloaddition cascade
    Shanahan, Charles S.
    Fang, Chao
    Paull, Daniel H.
    Martin, Stephen F.
    TETRAHEDRON, 2013, 69 (36) : 7592 - 7607
  • [2] Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
    Farid, Umar
    Aiello, Maria Luisa
    Connon, Stephen J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (43) : 10074 - 10079
  • [3] Catalytic asymmetric formal total syntheses of (+)- and (-)-cycloclavine
    Chaudhuri, Saikat
    Ghosh, Santanu
    Bhunia, Subhajit
    Bisai, Alakesh
    CHEMICAL COMMUNICATIONS, 2018, 54 (08) : 940 - 943
  • [4] Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones
    Gothelf, KV
    Jorgensen, KA
    CHEMICAL COMMUNICATIONS, 2000, (16) : 1449 - 1458
  • [5] Enantioselective Allylation of β-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin
    Koukal, Petr
    Ulc, Jan
    Necas, David
    Kotora, Martin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (12) : 2110 - 2114
  • [6] Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride
    Jarvis, Claire L.
    Hirschi, Jennifer S.
    Vetticatt, Mathew J.
    Seidel, Daniel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (10) : 2670 - 2674
  • [7] Catalytic enantioselective total syntheses of bisorbicillinolide, bisorbicillinol, and bisorbibutenolide
    Hong, R
    Chen, YG
    Deng, L
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) : 3478 - 3481
  • [8] Catalytic Aerobic Oxidation and Tandem Enantioselective Cycloaddition in Cascade Multicomponent Synthesis
    Potowski, Marco
    Merten, Christian
    Antonchick, Andrey P.
    Waldmann, Herbert
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (13) : 4913 - 4917
  • [9] Concise Total Synthesis of (-)-Quinocarcin Enabled by Catalytic Enantioselective Reductive 1,3-Dipolar Cycloaddition of Secondary Amides
    Ji, Kan-Lei
    He, Shu-Fan
    Xu, Dong-Dong
    He, Wen-Xin
    Zheng, Jian-Feng
    Huang, Pei-Qiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (25)
  • [10] Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition
    Hanari, Taiki
    Shimada, Naoyuki
    Kurosaki, Yasunobu
    Thrimurtulu, Neetipalli
    Nambu, Hisanori
    Anada, Masahiro
    Hashimoto, Shunichi
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (33) : 11671 - 11676