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
  • [111] RECENT RESEARCH IN MARINE NATURAL-PRODUCTS - PUUPEHENONES
    RAVI, BN
    PERZANOWSKI, HP
    ROSS, RA
    ERDMAN, TR
    SCHEUER, PJ
    FINER, J
    CLARDY, J
    [J]. PURE AND APPLIED CHEMISTRY, 1979, 51 (09) : 1893 - 1900
  • [112] Oxidative spiroacetalizations and spirolactonizations of arenes
    Rodríguez, S
    Wipf, P
    [J]. SYNTHESIS-STUTTGART, 2004, (17): : 2767 - 2783
  • [113] ANODIC OXIDATION OF PHENOLIC COMPOUNDS .2. PRODUCTS AND MECHANISM OF ANODIC OXIDATION OF HINDERED PHENOLS
    RONLAN, A
    PARKER, VD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (19): : 3214 - &
  • [114] Absolute configuration of scyphostatin
    Saito, S
    Tanaka, N
    Fujimoto, K
    Kogen, H
    [J]. ORGANIC LETTERS, 2000, 2 (04) : 505 - 506
  • [115] Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes.: Practical synthesis of enantioenriched terminal epoxides and 1,2-diols
    Schaus, SE
    Brandes, BD
    Larrow, JF
    Tokunaga, M
    Hansen, KB
    Gould, AE
    Furrow, ME
    Jacobsen, EN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1307 - 1315
  • [116] INTRAMOLECULAR OXIDATIVE COUPLING OF DIPHENOLIC, MONOPHENOLIC, AND NONPHENOLIC SUBSTRATES
    SCHWARTZ, MA
    ROSE, BF
    HOLTON, RA
    SCOTT, SW
    VISHNUVAJJALA, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) : 2571 - 2578
  • [117] SOGA O, 1984, CHEM LETT, P339, DOI 10.1246/cl.1984.339
  • [118] ISOLATION AND STRUCTURE OF A NEW NATURAL CYCLOPENTENONE DERIVATIVE FROM POTATO CULTURE SOLUTION OF PHOMA-WASABIAE YOKOGI
    SOGA, O
    IWAMOTO, H
    TAKUWA, A
    TAKATA, T
    TSUGIYAMA, Y
    HAMADA, K
    FUJIWARA, T
    NAKAYAMA, M
    [J]. CHEMISTRY LETTERS, 1988, (09) : 1535 - 1536
  • [119] PHENYLIODONIOPHENOLATES FROM 1,3-DIHYDROXYBENZENE DERIVATIVES
    SPYROUDIS, S
    TARANTILI, P
    [J]. TETRAHEDRON, 1994, 50 (39) : 11541 - 11552
  • [120] CHEMISTRY OF HOP CONSTITUENTS
    STEVENS, R
    [J]. CHEMICAL REVIEWS, 1967, 67 (01) : 19 - +