The application of a specific morphinan template to the synthesis of galanthamine

被引：11
作者：
Yamamoto, Naoshi [1 ]
Okada, Takahiro [2 ]
Harada, Yukimasa [3 ]
Kutsumura, Noriki [1 ]
Imaide, Satomi [3 ]
Saitoh, Tsuyoshi [1 ]
Fujii, Hideaki [3 ]
Nagase, Hiroshi [1 ,2 ,3 ]
机构：
[1] Univ Tsukuba, Int Inst Integrat Sleep Med WPI IIIS, I-1-1 Tennodai, Tsukuba, Ibaraki 3058575, Japan
[2] Univ Tsukuba, Grad Sch Pure & Appl Sci, I-1-1 Tennodai, Tsukuba, Ibaraki 3058571, Japan
[3] Kitasato Univ, Sch Pharm, Lab Med Chem, Minato Ku, 5-9-1 Shirokane, Tokyo 1088641, Japan
来源：
TETRAHEDRON | 2017年 / 73卷 / 39期
关键词：
Naltrexone; (-)-Galanthamine; Morphinan; Double C-C bond-cleavage; OPIOID RECEPTOR ANTAGONISTS; ASYMMETRIC TOTAL-SYNTHESIS; ALZHEIMERS-DISEASE; ACETYLCHOLINESTERASE INHIBITOR; FORMAL SYNTHESIS; (-)-GALANTHAMINE; DERIVATIVES; KAPPA; DESIGN; (-)-LYCORAMINE;
D O I：
10.1016/j.tet.2017.08.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(-)-Galanthamine (4) was synthesized from naltrexone (1) in 18 steps with 3% total yield by overcoming many specific side reactions derived from the 4,5-epoxymorphinan skeleton. The key features are cleavage of the D-ring by the Hofmann elimination and the following the one-pot C9-C10 and C9-14 bond cleavages concomitant with the C9 removal by the OsO4-NaIO4 combination reaction. Then, the treatment with zinc powder in acetic acid led to not only removal of the 2,2,2-trichloroethoxycarbonyl (Troc) group, but also reductive amination of the resulting imine to give the desired 7-membered ring. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5751 / 5758
页数：8
相关论文
共 59 条
  • [1] Probing Torpedo californica Acetylcholinesterase Catalytic Gorge with Two Novel Bis-functional Galanthamine Derivatives
    Bartolucci, Cecilia
    Haller, Lars A.
    Jordis, Ulrich
    Fels, Gregor
    Lamba, Doriano
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (02) : 745 - 751
  • [2] Carroll Fl, 1991, J CHEM SOC P1, V1, P3017
  • [3] Total Synthesis of (-)-Galanthamine and (-)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization
    Chen, Ji-Qiang
    Xie, Jian-Hua
    Bao, Deng-Hui
    Liu, Sheng
    Zhou, Qi-Lin
    [J]. ORGANIC LETTERS, 2012, 14 (11) : 2714 - 2717
  • [4] Asymmetric Synthesis of Bioactive Hydrodibenzofuran Alkaloids: (-)-Lycoramine, (-)-Galanthamine, and (+)-Lunarine
    Chen, Peng
    Bao, Xu
    Zhang, Le-Fen
    Ding, Ming
    Han, Xiao-Jie
    Li, Jing
    Zhang, Guo-Biao
    Tu, Yong-Qiang
    Fan, Chun-An
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (35) : 8161 - 8166
  • [5] Asymmetric Total Synthesis of (-)-Galanthamine via Intramolecular Heck Reaction of Conjugated Diene
    Choi, Juhee
    Kim, Hyunseok
    Park, Sangyun
    Tae, Jinsung
    [J]. SYNLETT, 2013, 24 (03) : 379 - 382
  • [6] DELANDER GE, 1984, J PHARMACOL EXP THER, V231, P91
  • [7] Dhawan BN, 1996, PHARMACOL REV, V48, P567
  • [8] Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate
    Endoma-Arias, Mary A. A.
    Hudlicky, Tomas
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) : 14540 - 14543
  • [9] Formal Synthesis of (±)-Galanthamine and (±)-Lycoramine Using Rh(I)-Catalyzed [(3+2)+1] Cycloaddition of 1-Ene-Vinylcyclopropane and CO
    Feng, Yu
    Yu, Zhi-Xiang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) : 1952 - 1956
  • [10] Practical procedures for the preparation of N-tert-butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides
    Furrow, ME
    Myers, AG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) : 5436 - 5445
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