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.
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页码:467 / 495
页数:29
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