Catalytic Asymmetric Synthesis of Benzobicyclo[3.2.1]octanes

被引:12
作者
Anif Pasha, Mohammed [1 ]
Peraka, Swamy [1 ]
Ramachary, Dhevalapally B. [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Catalysis Lab, Hyderabad 500046, India
关键词
asymmetric catalysis; 3+2] annulation; lawsone; methanobenzo[f]azulenes; organocatalysis; PHOTOCHEMICAL APPROACH; SKELETON;
D O I
10.1002/chem.202100985
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lawsone aldehydes were directly transformed into the biologically important, unique carbon skeleton of chiral methanobenzo[f]azulenes/methanodibenzo[a,d][7]annulenes in high dr and ee and in very good yields by using quinine-thiourea-catalyzed tandem Wittig/intramolecular Michael/intramolecular aldol reactions. This asymmetric catalytic tandem protocol will be highly useful because these final molecules are basic skeletons of important antibiotics.
引用
收藏
页码:10563 / 10568
页数:6
相关论文
共 48 条
  • [11] Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative
    Kikas, Ilijana
    Horvath, Otto
    Skoric, Irena
    [J]. TETRAHEDRON LETTERS, 2011, 52 (47) : 6255 - 6259
  • [12] Organocatalytic Asymmetric Formal [3+3]-Cycloaddition to Access 2,3-Diazaspiro[4.5]deca-3,6-dien-1-ones
    Krishna, A. Vamshi
    Reddy, G. Surendra
    Gorachand, B.
    Ramachary, Dhevalapally B.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (42) : 6623 - 6628
  • [13] Stereoselective Insertion of Benzynes into Lawsones: Synthesis of Biologically Important Benzannulated Bicyclo[3.3.0]octanes
    Kumar, A. Suresh
    Thirupathi, Guguloth
    Reddy, G. Surendra
    Ramachary, Dhevalapally B.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (05) : 1177 - 1183
  • [14] Catalytic Regioselective Benzoylation of 1,2-trans-Diols in Carbohydrates with Benzoyl Cyanide: The Axial Oxy Group Effect and the Action of Achiral and Chiral Amine Catalysts
    Li, Tianlu
    Li, Tong
    Linseis, Michael
    Wang, Fengshan
    Winter, Rainer F.
    Schmidt, Richard R.
    Peng, Peng
    [J]. ACS CATALYSIS, 2020, 10 (19) : 11406 - 11416
  • [15] Organocatalytic Atroposelective Intramolecular [4+2] Cycloaddition: Synthesis of Axially Chiral Heterobiaryls
    Liu, Yidong
    Wu, Xiaoyan
    Li, Shan
    Xue, Lu
    Shan, Chunhui
    Zhao, Zhengxing
    Yan, Hailong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) : 6491 - 6495
  • [16] Biosynthetically Guided Structure-Activity Relationship Studies of MerochlorinA, an Antibiotic Marine Natural Product
    Lopez-Perez, Borja
    Pepper, Henry P.
    Ma, Rong
    Fawcett, Benjamin J.
    Pehere, Ashok D.
    Wei, Qi
    Ji, Zengchun
    Polyak, Steven W.
    Dai, Huanqin
    Song, Fuhang
    Abell, Andrew D.
    Zhang, Lixin
    George, Jonathan H.
    [J]. CHEMMEDCHEM, 2017, 12 (23) : 1969 - 1976
  • [17] Biomimetic Synthesis of (±)-Merochlorin B
    Meier, Robin
    Strych, Sebastian
    Trauner, Dirk
    [J]. ORGANIC LETTERS, 2014, 16 (10) : 2634 - 2637
  • [18] Miles ZD, 2017, NAT CHEM, V9, P1235, DOI [10.1038/NCHEM.2829, 10.1038/nchem.2829]
  • [19] ORGANIC-PHOTOCHEMISTRY .67. PHOTOLYTIC CLEAVAGE OF REMOTE FUNCTIONAL-GROUPS IN POLYFUNCTIONAL MOLECULES - ACTIVATION OF A GAMMA-C-CL BOND IN THE ENDO-BENZOBICYCLO[3.2.1]OCTEN-3-YL AND EXO-BENZOBICYCLO[3.2.1]OCTEN-3-YL CHLORIDES
    MORRISON, H
    MUTHURAMU, K
    SEVERANCE, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) : 4681 - 4687
  • [20] Organocatalytic Reductive Propargylation: Scope and Applications
    Pasha, Mohammed Anif
    Krishna, A. Vamshi
    Ashok, Etikala
    Ramachary, Dhevalapally B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) : 15399 - 15416