Biomimetic Total Synthesis of Cruentaren A via Aromatization of Diketodioxinones

被引：47
|
作者：
Fouche, Marianne [1 ]
Rooney, Lisa [2 ]
Barrett, Anthony G. M. [1 ]
机构：
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] Novartis, Horsham RH12 5AB, W Sussex, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 07期
基金：
欧洲研究理事会;
关键词：
TRANSANNULAR AROMATIZATION; BYSSOVORAX-CRUENTA; NATURAL-PRODUCTS; ALCOHOLS; ACIDS; MACROCYCLIZATION; ORGANOBORANES; ALDEHYDES; ANALOGS; OLEFINS;
D O I：
10.1021/jo300225z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of cruentaren A, a biologically active resorcylate natural product, is reported. The aromatic unit was constructed via late-stage cyclization and aromatization from a diketodioxinone intermediate and macrocyclization using Furstner ring-closing alkyne metathesis.
引用
收藏
页码：3060 / 3070
页数：11
相关论文
共 50 条
  • [1] Total synthesis of cruentaren A
    Vintonyak, Viktor V.
    Maier, Martin E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5209 - 5211
  • [2] Concise total synthesis of cruentaren A
    Fuerstner, Alois
    Bindl, Martin
    Jean, Ludovic
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) : 9275 - 9278
  • [3] Total synthesis of cruentaren B
    Chakraborty, Tushar Kanti
    Chattopadhyay, Amit Kumar
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09): : 3578 - 3581
  • [4] Studies towards the Total Synthesis of Cruentaren B
    Yadav, Jhillu Singh
    Reddy, Ailuri Ramesh
    CHEMISTRYSELECT, 2018, 3 (43): : 12210 - 12212
  • [5] Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence
    Anderson, Katie
    Calo, Frederick
    Pfaffeneder, Toni
    White, Andrew J. P.
    Barrett, Anthony G. M.
    ORGANIC LETTERS, 2011, 13 (21) : 5748 - 5750
  • [6] A novel biomimetic synthesis of (S)-(-)-zearalenone: via macrocyclization and transannular aromatization
    Miyatake-Ondozabal, Hideki
    Barrett, Anthony G. M.
    TETRAHEDRON, 2010, 66 (33) : 6331 - 6334
  • [7] Total synthesis of thioamycolamide A via a biomimetic route
    Pan, Chengqian
    Kuranaga, Takefumi
    Kakeya, Hideaki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (41) : 8366 - 8370
  • [8] Synthesis of Cruentaren A
    Kusuma, Bhaskar Reddy
    Brandt, Gary E. L.
    Blagg, Brian S. J.
    ORGANIC LETTERS, 2012, 14 (24) : 6242 - 6245
  • [9] ATPase-Inhibitors archazolid and cruentaren: Total synthesis
    von Zezschwitz, Paultheo
    NACHRICHTEN AUS DER CHEMIE, 2008, 56 (05) : 535 - 540
  • [10] Total chemical synthesis of insulin via biomimetic folding
    Tofteng, A. P.
    Jensen, K. J.
    Hoeg-Jensen, T.
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 134 - 134
12345