Oxidative dearomatization of phenols:: Why, how and what for?

被引:417
作者
Quideau, Stephane
Pouysegu, Laurent
Deffieux, Denis
机构
[1] Univ Bordeaux 1, Inst Europeen Chim & Biol, F-33607 Pessac, France
[2] Inst Mol Sci, CNRS, UMR 5255, F-33405 Talence, France
关键词
oxidation; phenols; hypervalent iodine; dearomatization; Diels-Alder reaction;
D O I
10.1055/s-2008-1032094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This account reviews our investigations over the last ten I years on the selective dearomatization of phenols into cyclohexadienones and its application in natural products synthesis. 1 Introduction 2 The First Excavations: Oxocyclization and More... 2.1 Initial Observations on ortho-Quinol Acetate Chemistry 2.2 Total Synthesis of (+)-Puupehenone 3 Does It Work for Alkaloids? Azacyclization and More... 3.1 Nitrogen-Tethered ortho-Quinol Acetates 3.2 Applications in Alkaloid Synthesis 4 Dearomatization into Chiral ortho-Quinone Monoketals 5 What about Anodic Oxidation? 5.1 Anodic Spirocyclization into ortho-Quinone Ketals 5.2 A First Swing at Chiral ortho-Quinone Monoketals 6 The SIBX Success Story! 6.1 Before SIBX 6.2 After SIBX 7 Understanding Dimerization: Cieplak or Not Cieplak? 7.1 Total Synthesis of (+)-Aquaticol 7.2 Toward an All-Embracing Rationale! 8 Conclusions and Perspectives.
引用
收藏
页码:467 / 495
页数:29
相关论文
共 141 条
  • [41] PRODUCT AND MECHANISTIC STUDIES OF THE ANODIC-OXIDATION OF METHOXYLATED NAPHTHALENES - THE EECRCP MECHANISM
    DOLSON, MG
    SWENTON, JS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) : 2361 - 2371
  • [42] Biosynthesis of the Amaryllidaceae alkaloid galanthamine
    Eichhorn, J
    Takada, T
    Kita, Y
    Zenk, MH
    [J]. PHYTOCHEMISTRY, 1998, 49 (04) : 1037 - 1047
  • [43] Oxidative phenol coupling - tyrosine dimers and libraries containing tyrosyl peptide dimers
    Eickhoff, H
    Jung, G
    Rieker, A
    [J]. TETRAHEDRON, 2001, 57 (02) : 353 - 364
  • [44] THE X-RAY CRYSTAL-STRUCTURE AND ABSOLUTE-CONFIGURATION OF MAYTENOL, A REDUCTION PRODUCT OF THE BIS-DITERPENE MAYTENONE
    FALSHAW, CP
    KING, TJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08): : 1749 - 1752
  • [45] Finet J. P., 1998, Ligand Coupling Reactions with Heteroatomic Compounds
  • [46] Regio- and stereoselectivities in Diels-Alder cyclodimerizations of orthoquinonoid cyclohexa-2,4-dienones
    Gagnepain, Julien
    Mereau, Raphaeel
    Dejugnac, Delphine
    Leger, Jean-Michel
    Castet, Frederic
    Deffieux, Denis
    Pouysegu, Laurent
    Quideau, Stephane
    [J]. TETRAHEDRON, 2007, 63 (28) : 6493 - 6505
  • [47] Total synthesis of (+)-aquaticol by biomimetic phenol dearomatization:: Double diastereofacial differentiation in the Diels-Alder dimerization of orthoquinols with a C2-symmetric transition state
    Gagnepain, Julien
    Castet, Frederic
    Quideau, Stephane
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1533 - 1535
  • [48] Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene
    Gao, SY
    Ko, S
    Lin, YL
    Peddinti, RK
    Liao, CC
    [J]. TETRAHEDRON, 2001, 57 (02) : 297 - 308
  • [49] Biosynthesis of bitter acids in hops -: A 13C-NMR and 2H-NMR study on the building blocks of humulone
    Goese, M
    Kammhuber, K
    Bacher, A
    Zenk, MH
    Eisenreich, W
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1999, 263 (02): : 447 - 454
  • [50] CARBORANYLHALONIUM IONS - FROM STRIKING REACTIVITY TO A UNIFIED MECHANISTIC ANALYSIS OF POLAR REACTIONS OF DIARYLHALONIUM COMPOUNDS
    GRUSHIN, VV
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) : 529 - 536