A general synthesis of (+/-)-dibenzocyclooctadiene lignans

被引：0
|
作者：
Takeya, T [1 ]
Yamaki, S [1 ]
Itoh, T [1 ]
Hosogai, H [1 ]
Tobinaga, S [1 ]
机构：
[1] SHOWA COLL PHARMACEUT SCI, MACHIDA, TOKYO 194, JAPAN
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 1996年 / 44卷 / 05期
关键词：
general synthesis lignan; dibenzocyclooctadiene; spirodienone ether; Weitz' aminium salt; oxidative aryl-aryl coupling;
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
We have established a new general synthesis for (+/-)-dibenzocyclooctadiene lignans, including(+/-)-schizandrin (1a), (+/-)-gomisin A (1b), (+/-)-isoschizandrin (3a), and (+/-)-isogomisin A (3b), via the spiro-dienone ethers E- and T-11 as the key intermediates, prepared from the corresponding gisarylbutanol derivatives E- and T-10 by the oxidation with Weitz' aminium salt, tris(4-bromophenyl)aminium hexachloroantimonate (BAHA). These syntheses consist of 13 steps from the phenylpropanone 5.
引用
收藏
页码：909 / 918
页数：10
相关论文
共 50 条
  • [11] New dibenzocyclooctadiene lignans from the Kadsura ananosma
    Yang, Jian-Hong
    Zhang, Hai-Yan
    Du, Xue
    Wang, Wei
    Xiao, Wei-Lie
    Wen, Jin
    Pu, Jian-Xin
    Tang, Xi-Can
    Sun, Han-Dong
    TETRAHEDRON, 2011, 67 (25) : 4498 - 4504
  • [12] Dibenzocyclooctadiene Lignans from the Fruits of Schisandra viridis
    Tian, Tian
    Liu, Ye
    Yu, Heng-Yi
    Zhu, Yun-Yun
    Zhao, Xiao-Ya
    Ruan, Han-Li
    CHEMISTRY OF NATURAL COMPOUNDS, 2015, 51 (06) : 1046 - 1048
  • [13] ASYMMETRIC TOTAL SYNTHESIS OF DIBENZOCYCLOOCTADIENE LIGNANS (-)-SCHIZANDRIN AND (-)-ISOSCHIZANDRIN - STRUCTURE REVISION OF (+)-ISOSCHIZANDRIN
    WARSHAWSKY, AM
    MEYERS, AI
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8090 - 8099
  • [14] Dibenzocyclooctadiene lignans from the stems ofSchisandra sphaerandra
    Ying, You-Min
    Yu, Hang-Fei
    Rao, Gui-Wei
    Wang, Jian-Wei
    Shan, Wei-Guang
    Zhan, Zha-Jun
    NATURAL PRODUCT RESEARCH, 2022, 36 (01) : 287 - 294
  • [15] Dibenzocyclooctadiene Lignans from the Fruits of Schisandra viridis
    Tian Tian
    Ye Liu
    Heng-Yi Yu
    Yun-Yun Zhu
    Xiao-Ya Zhao
    Han-Li Ruan
    Chemistry of Natural Compounds, 2015, 51 : 1046 - 1048
  • [16] Cytotoxic dibenzocyclooctadiene lignans from Kadsura coccinea
    Zhao, Qing-Jie
    Song, Yan
    Chen, Hai-Sheng
    ARCHIVES OF PHARMACAL RESEARCH, 2014, 37 (11) : 1375 - 1379
  • [17] Cytotoxic dibenzocyclooctadiene lignans from Kadsura coccinea
    Qing-Jie Zhao
    Yan Song
    Hai-Sheng Chen
    Archives of Pharmacal Research, 2014, 37 : 1375 - 1379
  • [18] DIBENZOCYCLOOCTADIENE LIGNANS FROM KADSURA-JAPONICA
    OOKAWA, N
    IKEYA, Y
    SUGAMA, K
    TAGUCHI, H
    MARUNO, M
    PHYTOCHEMISTRY, 1995, 39 (05) : 1187 - 1191
  • [19] Catalyzed cyclizations leading to enrichment of functionality and chirality.: A general approach to dibenzocyclooctadiene lignans from α,ω-diynes
    Singidi, Ramakrishna Reddy
    RajanBabu, T. V.
    ORGANIC LETTERS, 2008, 10 (15) : 3351 - 3354
  • [20] Novel Bioactive Dibenzocyclooctadiene Lignans from Schisandra neglecta
    Gao, Xue-Mei
    Niu, De-Yun
    Meng, Chun-Yang
    Yao, Fu-Quan
    Zhou, Bin
    Wang, Rui-Rui
    Yang, Liu-Meng
    Zheng, Yong-Tang
    Hu, Qiu-Fen
    Sun, Han-Dong
    Xiao, Wei-Lie
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (12) : 2021 - +
12345