Total synthesis of (±)-ganocins B and C

被引：13
作者：
Liu, Yao [1 ]
Zhou, Chu-Jun [1 ]
Li, Qingjiang [1 ,2 ]
Wang, Honggen [1 ]
机构：
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 44期
基金：
中国国家自然科学基金;
关键词：
GOLD CATALYSIS; GANODERMA-LUCIDUM; POLYCYCLIC MEROTERPENOIDS; ANTIOXIDANT; POLYSACCHARIDES; ANTITUMOR; COCHLEAR; POTENT;
D O I：
10.1039/c6ob02049f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total synthesis of structurally unique polycyclic phenolic meroterpenoids, ganocins B and C is reported. The synthesis features gold-catalyzed intramolecular cascade cyclization to construct the C/D ring bearing an angular methyl group, diastereo-selective Michael addition, and acid-mediated one-pot Robinson cyclization/deprotection/isomerization.
引用
收藏
页码：10362 / 10365
页数：4
相关论文
共 31 条
  • [1] Purification, composition analysis and antioxidant activity of a polysaccharide from the fruiting bodies of Ganoderma atrum
    Chen, Yi
    Xie, Ming-Yong
    Nie, Shao-Ping
    Li, Chang
    Wang, Yuan-Xing
    [J]. FOOD CHEMISTRY, 2008, 107 (01) : 231 - 241
  • [2] Total Synthesis of (-)-Quinocarcin by Gold(I)-Catalyzed Regioselective Hydroamination
    Chiba, Hiroaki
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9169 - 9172
  • [3] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions
    Corma, A.
    Leyva-Perez, A.
    Sabater, Maria J.
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1657 - 1712
  • [4] Cochlearols A and B, Polycyclic Meroterpenoids from the Fungus Ganoderma cochlear That Have Renoprotective Activities
    Dou, Man
    Di, Lei
    Zhou, Li-Li
    Yan, Yong-Ming
    Wang, Xin-Long
    Zhou, Feng-Jiao
    Yang, Zhu-Liang
    Li, Rong-Tao
    Hou, Fan-Fan
    Cheng, Yong-Xian
    [J]. ORGANIC LETTERS, 2014, 16 (23) : 6064 - 6067
  • [5] Chemical features of Ganoderma polysaccharides with antioxidant, antitumor and antimicrobial activities
    Ferreira, Isabel C. F. R.
    Heleno, Sandrina A.
    Reis, Filipa S.
    Stojkovic, Dejan
    Queiroz, Maria Joao R. P.
    Helena Vasconcelos, M.
    Sokovic, Marina
    [J]. PHYTOCHEMISTRY, 2015, 114 : 38 - 55
  • [6] Acid catalysed rearrangements of 1-hydroxy-2,3,4,4a-tetrahydro-9H-xanthen-9-ones:: synthesis and cycloaddition reactions of 3,4-dihydro-9H-xanthen-9-ones
    Gabbutt, CD
    Hepworth, JD
    Urquhart, MWJ
    de Miguel, LMV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09): : 1547 - 1553
  • [7] Gold-catalyzed organic reactions
    Hashmi, A. Stephen K.
    [J]. CHEMICAL REVIEWS, 2007, 107 (07) : 3180 - 3211
  • [8] Gold catalysis in total synthesis
    Hashmi, A. Stephen K.
    Rudolph, Matthias
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (09) : 1766 - 1775
  • [9] Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
    Kirillova, Mariia S.
    Muratore, Michael E.
    Dorel, Ruth
    Echavarren, Antonio M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (11) : 3671 - 3674
  • [10] Total synthesis of wedelolactone
    Li, CC
    Xie, ZX
    Zhang, YD
    Chen, JH
    Yang, Z
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) : 8500 - 8504
1234