Total Synthesis of Epicoccin G

被引：76
作者：
Nicolaou, K. C. [1 ]
Totokotsopoulos, Sotirios
Giguere, Denis
Sun, Ya-Ping
Sarlah, David
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 21期
基金：
美国国家卫生研究院;
关键词：
CARBONYL-COMPOUNDS; GENERAL-APPROACH; DIKETOPIPERAZINES; METABOLITES; SPORIDESMIN; GLIOTOXIN; ALKALOIDS; PROLINE; NIGRUM; ACID;
D O I：
10.1021/ja2032635
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An expedient enantioselective total synthesis of epicoccin G and related dithiodiketopiperazines through a strategy featuring direct two-directional sulfenylation, photooxygenation, and Kornblum-DeLaMare rearrangement is described.
引用
收藏
页码：8150 / 8153
页数：4
相关论文
共 29 条
  • [1] BICYCLIC ENDOPEROXIDES AND SYNTHETIC APPLICATIONS
    BALCI, M
    [J]. CHEMICAL REVIEWS, 1981, 81 (01) : 91 - 108
  • [2] First synthesis of the antifungal oidiolactone C from trans-communic acid:: Cytotoxic and antimicrobial activity in podolactone-related compounds
    Barrero, AF
    Arseniyadis, S
    del Moral, JFQ
    Herrador, MM
    Valdivia, M
    Jiménez, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) : 2501 - 2508
  • [3] The biosynthetic origin of diketopiperazines derived from D-proline
    Bull, SD
    Davies, SG
    Parkin, RM
    Sánchez-Sancho, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15): : 2313 - 2320
  • [4] Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors
    DeLorbe, John E.
    Jabri, Salman Y.
    Mennen, Steven M.
    Overman, Larry E.
    Zhang, Fang-Li
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) : 6549 - 6552
  • [5] Pestalazines and Pestalamides, Bioactive Metabolites from the Plant Pathogenic Fungus Pestalotiopsis theae
    Ding, Gang
    Jiang, Lihua
    Guo, Liangdong
    Chen, Xulin
    Zhang, Hua
    Che, Yongsheng
    [J]. JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11): : 1861 - 1865
  • [6] TOTAL SYNTHESIS OF GLIOTOXIN
    FUKUYAMA, T
    KISHI, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) : 6723 - 6724
  • [7] FUKUYAMA T, 1974, TETRAHEDRON LETT, V15, P1549
  • [8] The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis
    Gardiner, DM
    Waring, P
    Howlett, BJ
    [J]. MICROBIOLOGY-SGM, 2005, 151 : 1021 - 1032
  • [9] Diketopiperazines from the Cordyceps-Colonizing Fungus Epicoccum nigrum
    Guo, Huijuan
    Sun, Bingda
    Gao, Hao
    Chen, Xulin
    Liu, Shuchun
    Yao, Xinsheng
    Liu, Xingzhong
    Che, Yongsheng
    [J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (12): : 2115 - 2119
  • [10] Diketopiperazines from Marine Organisms
    Huang, Riming
    Zhou, Xuefeng
    Xu, Tunhai
    Yang, Xianwen
    Liu, Yonghong
    [J]. CHEMISTRY & BIODIVERSITY, 2010, 7 (12) : 2809 - 2829
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