Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

被引：10
作者：
Zhong, Jiaxin [1 ]
He, Haibing [2 ]
Gao, Shuanhu [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 22期
基金：
中国国家自然科学基金;
关键词：
DAPHNIPHYLLUM ALKALOIDS; TRICYCLIC CORE; EXPEDIENT CONSTRUCTION; RING-SYSTEM; DAPHENYLLINE; CHEMISTRY; PROGRESS;
D O I：
10.1039/c9qo01111k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A-C ring as well as the spiro-A-C-E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.
引用
收藏
页码：3781 / 3785
页数：5
相关论文
共 61 条
  • [1] STUDIES DIRECTED AT THE SYNTHESIS OF OPTICALLY-ACTIVE PRETAZETTINE VIA INTRAMOLECULAR NITRONE ALKENE CYCLOADDITION REACTIONS
    BALDWIN, SW
    AUBE, J
    MCPHAIL, AT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6546 - 6550
  • [2] 1,3-Dipolar cycloaddition of nitrone-type dipoles to uncomplexed and metal-bound substrates bearing the CN triple bond
    Bokach, Nadezhda A.
    Kuznetsov, Maxim L.
    Kukushkin, Vadim Yu
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (23-24) : 2946 - 2967
  • [3] Chakraborty B., 2015, J CHEM PHARM RES, V7, P774
  • [4] Recent Progress in the Chemistry of Daphniphyllum Alkaloids
    Chattopadhyay, Amit Kumar
    Hanessian, Stephen
    [J]. CHEMICAL REVIEWS, 2017, 117 (05) : 4104 - 4146
  • [5] Total Synthesis of Isodaphlongamine H: A Possible Biogenetic Conundrum
    Chattopadhyay, Amit Kumar
    Vu Linh Ly
    Jakkepally, Shashidhar
    Berger, Gilles
    Hanessian, Stephen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) : 2577 - 2581
  • [6] Divergent Total Syntheses of (-)-Daphnilongeranin B and (-)-Daphenylline
    Chen, Xiaoming
    Zhang, Hai-Jun
    Yang, Xinkan
    Lv, Houqiang
    Shao, Xiaoru
    Tao, Cheng
    Wang, Huifei
    Cheng, Bin
    Li, Yun
    Guo, Jingjing
    Zhang, Jing
    Zhai, Hongbin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) : 947 - 951
  • [7] Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D
    Chen, Yu
    Zhang, Wenhao
    Ren, Lu
    Li, Jian
    Li, Ang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) : 952 - 956
  • [8] Synthesis of the Core Structure of Daphnimacropodines
    Chen, Yuye
    Hu, Jingping
    Guo, Lian-Dong
    Tian, Peilin
    Xu, Tianyue
    Xu, Jing
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 4309 - 4312
  • [9] A Concise Total Synthesis of (-)-HimalensineA
    Chen, Yuye
    Hu, Jingping
    Guo, Lian-Dong
    Zhong, Weihe
    Ning, Chengqing
    Xu, Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7390 - 7394
  • [10] Confalone N., 1988, ORG REACTIONS, V36, P1
1234567