First Total Synthesis of Arylnaphthalene Lignan Oleraisoindole A

被引:0
|
作者
Zhou, Weizeng [1 ]
Chen, Chenglong [1 ]
Sun, Shuyu [1 ]
Chu, Shanpeng [1 ]
Li, Mengying [1 ]
Xia, Yamu [1 ]
机构
[1] Qingdao Univ Sci & Technol, Dept Chem Engn, Qingdao 266042, Peoples R China
基金
中国国家自然科学基金;
关键词
Oleraisoindole A; Arylnaphthalene lignans; Electrocyclic reaction; Total synthesis; Lignans; OVERCROWDED MOLECULES; DERIVATIVES;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
First total synthesis of arylnaphthalene lignan Oleraisoindole A, isolated from Hyoscyamus niger, has been reported here. Oleraisoindole A has been known for its certain inhibitory effects on the growth of breast tumor cells and white blood cells. Therefore, we design a 13-step strategy to synthesize Oleraisoindole A, involving hydrolysis, dehydration, acylation, and Pd/C catalyzed hydrogenation. The structures of all compounds were confirmed by H-1 nuclear magnetic resonance (NMR), C-13 NMR, and high-resolution mass spectra. [GRAPHICS]
引用
收藏
页码:107 / 113
页数:7
相关论文
共 50 条
  • [31] 5-methoxyjusticidin A, a new arylnaphthalene lignan from Protium unifoliolatum
    Siani, AC
    Zoghbi, MDB
    Wolter, ELA
    Vencato, I
    JOURNAL OF NATURAL PRODUCTS, 1998, 61 (06): : 796 - 797
  • [32] First total synthesis of justicidone, a p-quinone-lignan derivative from Justicia hyssopifolia
    Boluda, CJ
    López, H
    Pérez, JA
    Trujillo, JM
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (08) : 930 - 933
  • [33] Synthesis of arylnaphthalene lignans
    Chirisa, Shingiria
    Feld, William A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [34] THE FIRST SYNTHESIS OF DIAXIAL BISLACTONE FUROFURAN LIGNAN
    YOSHIDA, S
    OHMIZU, H
    IWASAKI, T
    TETRAHEDRON LETTERS, 1995, 36 (45) : 8225 - 8226
  • [35] Toxicological Analysis of the Arylnaphthalene Lignan Justicidin B Using a Caenorhabditis elegans Model
    Sciandrone, Barbara
    Kentsop, Romeo Arago Dougue
    Pensotti, Roberta
    Ottolina, Gianluca
    Mascheretti, Iride
    Mattana, Monica
    Regonesi, Maria Elena
    MOLECULES, 2024, 29 (23):
  • [36] Patavine, a new arylnaphthalene lignan glycoside from shoot cultures of Haplophyllum patavinum
    Innocenti, G
    Puricelli, L
    Piacente, S
    Caniato, R
    Filippini, R
    Cappelletti, EM
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (06) : 844 - 846
  • [37] TOTAL SYNTHESIS OF ANTI-LEUKEMIC LIGNAN (+/-)-STEGANACIN
    BECKER, D
    HUGHES, LR
    RAPHAEL, RA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (14): : 1674 - 1681
  • [38] Total synthesis of vibsanol, a benzofuran-type lignan
    Sakai, A
    Aoyama, T
    Shioiri, T
    TETRAHEDRON LETTERS, 1999, 40 (22) : 4211 - 4214
  • [39] Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products
    Coleman, RS
    Gurrala, SR
    Mitra, S
    Raao, A
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22): : 8932 - 8941
  • [40] An asymmetric route to total synthesis of the furano lignan (+)-veraguensin
    Matcha, Kiran
    Ghosh, Subrata
    TETRAHEDRON LETTERS, 2010, 51 (52) : 6924 - 6927