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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Bibliographic Details
Published in:Synlett 2008-03, Vol.2008 (4), p.467-495
Main Authors: Quideau, Stéphane, Pouységu, Laurent, Deffieux, Denis
Format: Article
Language:English
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Summary: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
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2008-1032094