Asymmetric synthesis of the tetracyclic core of bufogargarizin C by an intramolecular [5+2] cycloaddition

被引:10
|
作者
Fan, Jian-Hong [1 ,2 ,3 ]
Hu, Ya-Jian [1 ,2 ,3 ]
Guo, Qiang [2 ,3 ]
Li, Shaoping [1 ]
Zhao, Jing [1 ]
Li, Chuang-Chuang [2 ,3 ]
机构
[1] Univ Macau, Inst Chinese Med Sci, Macau, Peoples R China
[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[3] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; CONVERGENT TOTAL-SYNTHESIS; STEROIDS; OUABAGENIN; CARDENOLIDE; GLYCOSIDES; REDUCTION; ALKALOIDS; ETHERS;
D O I
10.1039/c8qo01089g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise asymmetric synthesis of the core of bufogargarizin C, which contains a synthetically challenging 7/5/6/5-tetracyclic ring system, is reported. This approach features a unique BrOnsted acid-mediated intramolecular [5 + 2] cycloaddition, which is the first example of intramolecular [5 + 2] cycloaddition of an allene moiety mediated by acid.
引用
收藏
页码:22 / 26
页数:5
相关论文
共 50 条
  • [21] Asymmetric oxidopyrylium-alkene[5+2] cycloaddition: a divergent approach for the synthesis of enantiopure oxabicyclo[5.4.0]undecanes
    Krishna, UM
    Deodhar, KD
    Trivedi, GK
    TETRAHEDRON, 2004, 60 (22) : 4829 - 4836
  • [22] Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5+2] cycloaddition of allenes and vinylcyclopropanes
    Wender, PA
    Zhang, L
    ORGANIC LETTERS, 2000, 2 (15) : 2323 - 2326
  • [23] Synthesis of Oxa-B-Ring Analogs of Colchicine through Rh-Catalyzed Intramolecular [5+2] Cycloaddition
    Termath, Andreas Ole
    Ritter, Stefanie
    Koenig, Marcel
    Kranz, Darius Paul
    Neudoerfl, Joerg-Martin
    Prokop, Aram
    Schmalz, Hans-Guenther
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) : 4501 - 4507
  • [24] An efficient Rh-catalyst system for the intramolecular [4+2] and [5+2] cycloaddition reactions
    Wang, B
    Cao, P
    Zhang, XM
    TETRAHEDRON LETTERS, 2000, 41 (42) : 8041 - 8044
  • [25] A sulfinyl-directed asymmetric [5C+2C] intramolecular acetoxypyranone-alkene cycloaddition
    López, F
    Castedo, L
    Mascareñas, JL
    ORGANIC LETTERS, 2002, 4 (21) : 3683 - 3685
  • [26] Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition
    Wang, Lu
    Xu, Chen
    Chen, Li
    Hao, Xiaojiang
    Wang, David Zhigang
    ORGANIC LETTERS, 2014, 16 (04) : 1076 - 1079
  • [27] Asymmetric oxidopyrylium-alkene [5+2] cycloaddition: Synthesis of enantiopure oxa-bridged bicyclo[5.4.0]undecanes
    Krishna, UM
    Srikanth, GSC
    Trivedi, GK
    Deodhar, KD
    SYNLETT, 2003, (15) : 2383 - 2385
  • [28] Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids
    Carra, Ryan J.
    Epperson, Matthew T.
    Gin, David Y.
    TETRAHEDRON, 2008, 64 (17) : 3629 - 3641
  • [29] Highly Diastereoselective Intramolecular Asymmetric Oxidopyrylium-olefin [5+2] Cycloaddition and Synthesis of 8-Oxabicyclo[3.2.1]oct-3-enone Containing Ring Systems
    Ghosh, Arun K.
    Yadav, Monika
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (12): : 8127 - 8142
  • [30] Tandem 5+2/3+2 and 5+2/3+3 cycloaddition reactions
    Engler, TA
    Scheibe, CM
    Iyengar, R
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24): : 8274 - 8275