Total Syntheses of Phleghenrines A and C

被引：2
|
作者：
Cai, Xinpei [1 ,2 ]
Li, Lei [1 ,2 ,3 ]
Wang, Ye-Cheng [1 ,2 ]
Zhou, Jianhan [1 ,2 ]
Dai, Mingji [1 ,2 ,3 ]
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] Purdue Univ, Ctr Canc Res, W Lafayette, IN 47907 USA
[3] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 28期
关键词：
MASKED O-BENZOQUINONES; LYCOPODIUM ALKALOIDS; EFFICIENT SYNTHESIS; LYCONADINS; HUPERZINE;
D O I：
10.1021/acs.orglett.3c01784
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the total syntheses of phleghenrinesA and Cfrom commercially available starting materials in 7 and 8 steps, respectively.Notable steps include an inverse electron-demand Diels-Alderreaction between a masked o-benzoquinone and a N-protected enamine to prepare one key intermediate witha bicyclo[2.2.2]octenone core, a Bu''chner-Curtius-Schlotterbeckone-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone,and Trauner's modified 2-pyridone synthesis to install the2-pyridone moiety.
引用
收藏
页码：5258 / 5261
页数：4
相关论文
共 50 条
  • [41] First total syntheses of (-)-macrosphelides J and K and elucidation of their absolute configuration
    Yun, Hwayoung
    Paek, Seung-Mann
    Jung, Jong-Wha
    Kim, Nam-Jung
    Kim, Seok-Ho
    Suh, Young-Ger
    CHEMICAL COMMUNICATIONS, 2009, (18) : 2463 - 2465
  • [42] Stereocontrolled Total Syntheses of (±)-Fawcettimine, (±)-Lycoflexine, and (±)-Lycoflexine N-Oxide
    Xu, Ke
    Cheng, Bin
    Li, Yun
    Xu, Tingting
    Yu, Cunming
    Zhang, Jun
    Ma, Zhiqiang
    Zhai, Hongbin
    ORGANIC LETTERS, 2014, 16 (01) : 196 - 199
  • [43] Concise Total Syntheses of (±)-Joubertiamine, (±)-O-Methyljoubertiamine, (±)-3′-Methoxy-4'-O-methyljoubertiamine, (±)-Mesembrane, and (±)-Crinane
    Das, Mrinal Kanti
    De, Subhadip
    Shubhashish
    Bisai, Alakesh
    SYNTHESIS-STUTTGART, 2016, 48 (13): : 2093 - 2104
  • [44] Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides
    Boukouvalas, John
    Bruneau-Latour, Nicolas
    SYNLETT, 2013, 24 (20) : 2691 - 2694
  • [45] Total Syntheses of Lycoposerramine-V and 5-epi-Lycoposerramine-V
    Zhang, Lan-De
    Zhou, Ting-Ting
    Qi, Sen-Xing
    Xi, Jie
    Yang, Xiao-Liang
    Yao, Zhu-Jun
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (10) : 2740 - 2744
  • [46] Total Synthesis of Ningalin C
    Kim, Woo-Hyung
    Kim, Jang-Yeop
    Cho, Cheon-Gyu
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (12): : 1463 - 1466
  • [47] Total Synthesis of Brasilicardins A and C
    Anada, Masahiro
    Hanari, Taiki
    Kakita, Kosuke
    Kurosaki, Yasunobu
    Katsuse, Kazuki
    Sunadoi, Yuta
    Jinushi, Yu
    Takeda, Koji
    Matsunaga, Shigeki
    Hashimoto, Shunichi
    ORGANIC LETTERS, 2017, 19 (20) : 5581 - 5584
  • [48] Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide
    Exner, Claudia J.
    Laclef, Sylvain
    Poli, Florent
    Turks, Maris
    Vogel, Pierre
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03) : 840 - 845
  • [49] Unified Total Syntheses of Fawcettimine Class Alkaloids: Fawcettimine, Fawcettidine, Lycoflexine, and Lycoposerramine B
    Pan, Guojun
    Williams, Robert M.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (10) : 4801 - 4811
  • [50] Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2
    Nathel, Noah F. Fine
    Shah, Tejas K.
    Bronner, Sarah M.
    Garg, Neil K.
    CHEMICAL SCIENCE, 2014, 5 (06) : 2184 - 2190
12345