Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

被引：34
|
作者：
Anderson, Katie [1 ]
Calo, Frederick [1 ]
Pfaffeneder, Toni [1 ]
White, Andrew J. P. [1 ]
Barrett, Anthony G. M. [1 ]
机构：
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 21期
基金：
英国工程与自然科学研究理事会;
关键词：
CONVERGENT SYNTHESIS; NATURAL-PRODUCTS; DERIVATIVES; ALLYLATION; COMPLEXES; LACTONES; ACIDS;
D O I：
10.1021/ol202320m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.
引用
收藏
页码：5748 / 5750
页数：3
相关论文
共 50 条
  • [21] Biomimetic Total Synthesis of Cruentaren A via Aromatization of Diketodioxinones
    Fouche, Marianne
    Rooney, Lisa
    Barrett, Anthony G. M.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3060 - 3070
  • [22] First total synthesis of (±)-Linoxepin via a palladium-catalyzed domino reaction
    Schild, Svenia C.
    Clerc, Jerme
    Tietze, Lutz F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [23] First total synthesis of Dysidavarone A via an intramolecular palladium-catalyzed α-arylation
    Schmalzbauer, Bjoern
    Herrmann, Jennifer
    Mueller, Rolf
    Menche, Dirk
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [24] Total synthesis of (+)-camptothecin via an intramolecular palladium-catalyzed cyclization strategy
    Chavan, Subhash P.
    Pathak, Ashok B.
    Kalkote, Uttam R.
    SYNLETT, 2007, (17) : 2635 - 2638
  • [25] Palladium-Catalyzed Intramolecular Dearomatization of Indoles via Decarboxylative Alkynyl Termination
    Chen, Si
    Wu, Xin-Xing
    Wang, Jia
    Hao, Xin-Hua
    Xia, Yu
    Shen, Yi
    Jing, Huanwang
    Liang, Yong-Min
    ORGANIC LETTERS, 2016, 18 (16) : 4016 - 4019
  • [26] Palladium-catalyzed couplings to nucleophilic heteroarenes: the total synthesis of (-)-frondosin B
    Hughes, CC
    Trauner, D
    TETRAHEDRON, 2004, 60 (43) : 9675 - 9686
  • [27] Pyrosulfite-Involved Synthesis of Sulfides by Palladium-Catalyzed Decarboxylative Couplings
    Li, Xiaokang
    Wei, Bei
    Gong, Yanlong
    Li, Chengyi
    Liu, Xiaoting
    Liu, Bin
    Li, Qingshan
    Ban, Shurong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 10282 - 10286
  • [28] Palladium-Catalyzed Decarboxylative Arylation of Benzoylacrylic Acids toward the Synthesis of Chalcones
    Unoh, Yuto
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10): : 5096 - 5102
  • [29] Palladium-Catalyzed α-Arylation Reactions in Total Synthesis
    Sivanandan, Sudheesh T.
    Shaji, Ashna
    Ibnusaud, Ibrahim
    Seechurn, Carin C. C. Johansson
    Colacot, Thomas J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (01) : 38 - 49
  • [30] Palladium-Catalyzed Oxidative Aminocarbonylation by Decarboxylative Coupling: Synthesis of Alkynyl Amides
    Hwang, Jinil
    Choi, Jinseop
    Park, Kyungho
    Kim, Wonyoung
    Song, Kwang Ho
    Lee, Sunwoo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (10) : 2235 - 2243
12345