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Synlett 2008(4): 467-495
DOI: 10.1055/s-2008-1032094
DOI: 10.1055/s-2008-1032094
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Oxidative Dearomatization of Phenols: Why, How and What For?
Further Information
Received
29 September 2007
Publication Date:
12 February 2008 (online)
Publication History
Publication Date:
12 February 2008 (online)
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
Key words
oxidation - phenols - hypervalent iodine - dearomatization - Diels-Alder reaction
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