Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

被引:0
作者
Imaoka, Sho [1 ]
Nakashima, Yuta [1 ]
Kitajima, Mariko [1 ]
Ishikawa, Hayato [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, 1-8-1 Inohana,Chuo Ku, Chiba 2608675, Japan
关键词
bioinspired reaction; total synthesis; oxindole alkaloid; cascade reaction; Kopsia alkaloid; INDOLE ALKALOIDS; RECENT PROGRESS; CHEMISTRY;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The first enantioselective total synthesis of kopsiyunnanine B, which has a unique folded and complex pentacyclic structure containing six contiguous chiral centers, has been achieved along our originally proposed biosynthetic pathway. The key reaction of this synthesis includes a bioinspired cascade that builds three ring structures and three chiral centers in one step and features the stereoselective reduction of a beta-acrylate and oxidation to an oxindole.
引用
收藏
页码:68 / 74
页数:7
相关论文
共 50 条
  • [31] Total Synthesis of Sarpagine Alkaloid (-)-Normacusine B
    Zhu, Jianquan
    Zhang, Chao
    Liu, Luyi
    Xue, Chaoyun
    Cai, Yukun
    Liu, Xiao-Yu
    Xue, Fei
    Qin, Yong
    ORGANIC LETTERS, 2022, 24 (19) : 3515 - 3520
  • [32] Divergent Asymmetric Total Synthesis of (-)-Voacafricines A and B
    Andres, Remi
    Wang, Qian
    Zhu, Jieping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (16)
  • [33] Total Synthesis and Structural Revision of Viridicatumtoxin B
    Nicolaou, K. C.
    Nilewski, Christian
    Hale, Christopher R. H.
    Ioannidou, Heraklidia A.
    ElMarrouni, Abdelatif
    Koch, Lizanne G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8736 - 8741
  • [34] Bioinspired and Concise Synthesis of (±)-Stemoamide
    Wang, Yan
    Zhu, Lili
    Zhang, Yuying
    Hong, Ran
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) : 2787 - 2790
  • [35] Total Synthesis of (+)-MPC1001B
    Kurogi, Taichi
    Okaya, Shun
    Fujiwara, Hideto
    Okano, Kentaro
    Tokuyama, Hidetoshi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) : 283 - 287
  • [36] Bioinspired Total Synthesis of (-)-Vescalin: A Nonahydroxytriphenoylated C-Glucosidic Ellagitannin
    Richieu, Antoine
    Peixoto, Philippe A.
    Pouysegu, Laurent
    Deffieux, Denis
    Quideau, Stephane
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) : 13833 - 13837
  • [37] Studies of a Diazo Cyclopropanation Strategy for the Total Synthesis of (-)-LundurineA
    Huang, Hong-Xiu
    Jin, Shuai-Jiang
    Gong, Jin
    Zhang, Dan
    Song, Hao
    Qin, Yong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (38) : 13284 - 13290
  • [38] Bioinspired Total Syntheses of Gymnothelignans
    Hong, Xiaoling
    Chen, Peng
    Li, Huilin
    She, Xuegong
    SYNLETT, 2024, 35 (05) : 535 - 542
  • [39] Total Synthesis of (+)-Eburnamonine
    Prasad, Kavirayani R.
    Nidhiry, John E.
    SYNLETT, 2012, (10) : 1477 - 1480
  • [40] Total Synthesis of Hirsutellone B
    Nicolaou, K. C.
    Sarlah, David
    Wu, T. Robert
    Zhan, Weiqiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6870 - 6874