Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids

被引:1
|
作者
Abranyi-Balogh, Peter [1 ]
Foeldesi, Tamas [1 ]
Milen, Matyas [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Budapest, Hungary
来源
MONATSHEFTE FUR CHEMIE | 2015年 / 146卷 / 11期
关键词
Natural products; Heterocycles; Catalysis; Thionation; Liebeskind-Srogl reaction; BETA-CARBOLINE DERIVATIVES; CRYPTOSTYLIS FULVA SCHLTR; ANTI-HIV AGENTS; ORCHIDACEAE ALKALOIDS; ABSOLUTE CONFIGURATION; ASYMMETRIC-SYNTHESIS; TETRAHYDROISOQUINOLINES; CYCLIZATION; ANTAGONISTS; ANALOGS;
D O I
10.1007/s00706-015-1564-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new synthetic route was developed for the preparation of natural products cryptostyline I, II, III and 1-phenyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. The Liebeskind-Srogl palladium-catalyzed carbon-carbon cross-coupling protocol was used in the key step of the total synthesis. [GRAPHICS] .
引用
收藏
页码:1907 / 1912
页数:6
相关论文
共 50 条
  • [1] Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids
    Péter Ábrányi-Balogh
    Tamás Földesi
    Mátyás Milen
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 1907 - 1912
  • [2] AN IMPROVED SYNTHESIS OF VARIOUS RACEMIC POLYPHENOLIC TETRAHYDROISOQUINOLINE ALKALOIDS
    TEITEL, S
    BROSSI, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (06) : 825 - &
  • [3] 1-aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
    Cheng, Pi
    Huang, Ning
    Jiang, Zhi-Yong
    Zhang, Quan
    Zheng, Yong-Tang
    Chen, Ji-Jun
    Zhang, Xue-Mei
    Ma, Yun-Bao
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) : 2475 - 2478
  • [4] Progress in the Total Synthesis of Antitumor Tetrahydroisoquinoline Alkaloids
    Gao, Yi
    Tu, Ni
    Liu, Xiaoting
    Lu, Kangkang
    Chen, Siyu
    Guo, Ju
    CHEMISTRY & BIODIVERSITY, 2023, 20 (05)
  • [5] Stereoselective total synthesis of enantiomerically pure 1-trifluoromethyl tetrahydroisoquinoline alkaloids
    Bravo, P
    Crucianelli, M
    Farina, A
    Meille, SV
    Volonterio, A
    Zanda, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (03) : 435 - 440
  • [6] Recent Advances in Total Synthesis of Tetrahydroisoquinoline Alkaloids Quinocarcin and Lemonomycin
    Guo, Ju
    Yang, Yang
    Shen, Lanhua
    Li, Jingyi
    Li, Fuan
    Wang, Sifan
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2024, 21 (08) : 852 - 861
  • [7] Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines: Access to Valuable Chiral 1-Aryl-Tetrahydroisoquinoline Scaffolds
    Wu, Zi
    Perez, Marc
    Scalone, Michelangelo
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) : 4925 - 4928
  • [8] Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002-2020)
    Kim, Alexia N.
    Ngamnithiporn, Aurapat
    Du, Emily
    Stoltz, Brian M.
    CHEMICAL REVIEWS, 2023, 123 (15) : 9447 - 9496
  • [9] Quantitative structure-activity relationship studies on 1-aryl-tetrahydroisoquinoline analogs as active anti-HIV agents
    Chen, Ke-xian
    Xie, Hai-ying
    Li, Zu-guang
    Gao, Jian-rong
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) : 5381 - 5386
  • [10] SCELETIUM (AIZOACEAE) ALKALOIDS - TOTAL SYNTHESIS OF RACEMIC MESEMBRANONE, JOUBERTINAMINE AND EPIJOUBERTINAMINE
    SANCHEZ, IH
    SORIA, JD
    LARRAZA, MI
    FLORES, HJ
    TETRAHEDRON LETTERS, 1983, 24 (06) : 551 - 554