Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel-Mediated Cyclization of Tryptamine-Ynamide

被引：0
|
作者：
Han, Changhong [1 ,2 ,3 ]
Yang, Lu [1 ,2 ,3 ]
Yao, Kaizong [1 ,2 ,3 ]
Zhang, Sen [1 ,2 ,3 ]
Fu, Jiayue [1 ,2 ,3 ]
Sun, Hanyang [1 ,2 ,3 ]
Xu, Hongsheng [4 ]
Lin, Bin [1 ,2 ,3 ]
Cheng, Maosheng [1 ,3 ]
Liu, Yongxiang [1 ,2 ,3 ]
机构：
[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Liaoning, Peoples R China
[2] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Liaoning, Peoples R China
[3] Inst Drug Res Med Capital China, Benxi 117000, Liaoning, Peoples R China
[4] Zhejiang Shapuaisi Pharmaceut Co Ltd, Hangzhou 314299, Zhejiang, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 12期
基金：
中国博士后科学基金; 中国国家自然科学基金;
关键词：
Asymmetric synthesis; Alkaloids; Dihydrospirotryprostatin B; Tryptamine-ynamide; Cross-coupling; Silica gel-mediated cyclization; Oxidation; MAMMALIAN-CELL CYCLE; SPIROTRYPROSTATIN-B; ASPERGILLUS-FUMIGATUS; TANDEM CYCLIZATIONS; CONCISE; (-)-SPIROTRYPROSTATIN-B; INHIBITORS;
D O I：
10.1002/cjoc.202300727
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps (8 purifications) from L-tryptophan. The main feature of our synthetic strategy is the efficient construction of spirocyclic oxindole intermediate containing a chiral quaternary carbon center, involving the silica gel-mediated cyclization of tryptamine-ynamide and oxidation under neat conditions.
引用
收藏
页码：1355 / 1359
页数：5
相关论文
共 41 条
  • [1] Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide
    Yang, Lu
    Huang, Siwen
    Huang, Rongkang
    Hou, Anbin
    Zhang, Sen
    Su, Hongwei
    Ding, Xiaohong
    Lin, Bin
    Cheng, Maosheng
    Liu, Yongxiang
    ORGANIC LETTERS, 2021, 23 (16) : 6471 - 6476
  • [2] BiCl3-Mediated Tandem Cyclization of Tryptamine-Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives
    Lin, Xiao-Tong
    Zhao, Cheng
    Wang, Da-Ru
    Wu, Guang-Cheng
    Chen, Guo-Shu
    Chen, Shu-Jie
    Ren, Hai
    Deng, Dong-Sheng
    Xu, Yi-Bing
    Hu, Xiao-Wei
    Liu, Yun-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (04) : 890 - 896
  • [3] Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes
    Serra-Muns, Anna
    Guerinot, Amandine
    Reymond, Sebastien
    Cossy, Janine
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4178 - 4180
  • [4] Silica gel-Mediated Friedel-Crafts Reaction of lndoles with Functionalized Nitroallylic Acetates via an SN1 Process
    Ho, Ching-Yin
    Roy, Suparna
    Chen, Yan-Ming
    Chen, Kwunmin
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2012, 59 (08) : 940 - 946
  • [5] Silica Gel-Mediated Amide Bond Formation: An Environmentally Benign Method for Liquid-Phase Synthesis and Cytotoxic Activities of Amides
    Yang, Xiao-Dong
    Zeng, Xiang-Hui
    Zhao, Yuan-Hong
    Wang, Xue-Quan
    Pan, Zhi-Qiang
    Li, Liang
    Zhang, Hong-Bin
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (03): : 307 - 310
  • [6] Silica Gel-mediated Synthesis of β-Enamino Esters and its Application for the Synthesis of Indeno 4-Hydroxypyridin-2(1H)-Ones
    Kim, Soong-Hyun
    Bae, Seri
    Ko, Eun Bi
    Park, Ga Young
    Lee, Eunhye
    Hwang, Hee Jong
    Im, Chun Young
    Song, Minsoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2019, 40 (03) : 262 - 269
  • [7] Silica gel-mediated microwave-assisted efficient synthesis of highly substituted imidazoles and exploration of naked eye/colorimetric sensor for anions
    Bhattacharyya, Pranabes
    Medda, Arunima
    Samanta, Anuva
    Guchhait, Nikhil
    Das, Asish R.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2011, 88 (07) : 983 - 993
  • [8] Rapid synthesis of azepinoindole derivatives from tryptamine sulfonamides and bromoallyl sulfones via an acid-mediated cyclization and rearrangement
    Gurram, Ravikumar
    Nanubolu, Jagadeesh Babu
    Menon, Rajeev S.
    CHEMICAL COMMUNICATIONS, 2021, 57 (05) : 635 - 638
  • [9] A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization
    Smith, Myles W.
    Zhou, Zhiyao
    Gao, Alison X.
    Shimbayashi, Takuya
    Snyder, Scott A.
    ORGANIC LETTERS, 2017, 19 (05) : 1004 - 1007
  • [10] Total Synthesis of (-)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2+2+2] Cyclization between Ynamide and Diynes
    Saito, Nozomi
    Ichimaru, Taisuke
    Sato, Yoshihiro
    ORGANIC LETTERS, 2012, 14 (07) : 1914 - 1917
12345