Oxidative Dearomatization of Phenols: Why, How and What For?

Abstract This account reviews our investigations over the last ten 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 A...

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Published in:Synlett 2008-03, Vol.2008 (4), p.467-495
Main Authors: Quideau, Stéphane, Pouységu, Laurent, Deffieux, Denis
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creator Quideau, Stéphane
Pouységu, Laurent
Deffieux, Denis
description Abstract This account reviews our investigations over the last ten 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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title Oxidative Dearomatization of Phenols: Why, How and What For?
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