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
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
  • [31] Transformations of lignans. Part 4: Oxidative and reductive rearrangements of dibenzocyclooctadiene and spirodienone lignans
    Venkateswarlu, R
    Kamakshi, C
    Moinuddin, SGA
    Subhash, PV
    Ward, RS
    Pelter, A
    Coles, SJ
    Hursthouse, MB
    Light, ME
    TETRAHEDRON, 2001, 57 (26) : 5625 - 5632
  • [32] Dibenzocyclooctadiene Lignans from Kadsura polysperma and Their Antineurodegenerative Activities
    Dong, Ke
    Pu, Jian-Xin
    Zhang, Hai-Yan
    Du, Xue
    Li, Xiao-Nian
    Zou, Juan
    Yang, Jian-Hong
    Zhao, Wei
    Tang, Xi-Can
    Sun, Han-Dong
    JOURNAL OF NATURAL PRODUCTS, 2012, 75 (02): : 249 - 256
  • [33] Four new dibenzocyclooctadiene lignans from Schisandra rubriflora
    Li, Hong-Mei
    Luo, Yong-Ming
    Pu, Jian-Xin
    Li, Xiao-Nian
    Lei, Chun
    Wang, Rui-Rui
    Zheng, Yong-Tang
    Sun, Han-Dong
    Li, Rong-Tao
    HELVETICA CHIMICA ACTA, 2008, 91 (06) : 1053 - 1062
  • [34] Hepatoprotective dibenzocyclooctadiene lignans from the fruits of Kadsura coccinea
    Wu, Wenming
    Liu, Jian
    Ruan, Hanli
    Jin, An
    FITOTERAPIA, 2024, 178
  • [35] 3 NEW DIBENZOCYCLOOCTADIENE LIGNANS FROM KADSURA-LONGIPEDUNCULATA
    LI, LN
    XUE, H
    LI, X
    PLANTA MEDICA, 1991, 57 (02) : 169 - 171
  • [36] SYNTHESIS OF (+/-)-DIBENZOCYCLOOCTADIENE LIGNANS, (+/-)-SCHIZANDRIN, (+/-)-GOMISIN-A AND THEIR STEREOISOMERS, UTILIZING THE SAMARIUM-GRIGNARD REACTION
    TAKEYA, T
    OHGUCHI, A
    ARA, Y
    TOBINAGA, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (03) : 430 - 437
  • [37] C18 dibenzocyclooctadiene lignans from Kadsura philippinensis
    Shen, Ya-Ching
    Liaw, Chia-Ching
    Cheng, Yuan-Bin
    Ahmed, Atallah F.
    Lai, Mei-Chou
    Liou, Shorong-Shii
    Wu, Tian-Shung
    Kuo, Yao-Haur
    Lin, Yu-Chi
    JOURNAL OF NATURAL PRODUCTS, 2006, 69 (06): : 963 - 966
  • [38] Three bioactive dibenzocyclooctadiene lignans from the fruits of Kadsura coccinea
    Wu, Wen-Ming
    Liu, Jian
    Chen, Chao
    Wang, Bao-Lin
    Jin, An
    NATURAL PRODUCT RESEARCH, 2025,
  • [39] DIBENZOCYCLOOCTADIENE LIGNANS FROM ROOTS AND STEMS OF KADSURA-COCCINEA
    LI, LN
    XUE, H
    TAN, R
    PLANTA MEDICA, 1985, 51 (04) : 297 - 300
  • [40] CARBONIUM CYCLIZATION—STUDIES ON LIGNANS CONTAINING THE DIBENZOCYCLOOCTADIENE SYSTEM.Ⅰ
    Rui TAN Qi Tai ZHENG Cun Heng HE Xiao Tian LIANG Institute of Materia Medica
    Chinese Chemical Letters, 1990, (01) : 47 - 48