Journal
SYNLETT
Volume -, Issue 4, Pages 467-495Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2008-1032094
Keywords
oxidation; phenols; hypervalent iodine; dearomatization; Diels-Alder reaction
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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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