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Synlett 2002(4): 0533-0543
DOI: 10.1055/s-2002-22696
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© Georg Thieme Verlag Stuttgart · New York

Anodic Oxidation of Phenols Towards the Synthesis of Bioactive Natural
Products

Shosuke Yamamura*, Shigeru Nishiyama*
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan
Fax: +81(45)5661717; e-Mail: yamamura@chem.keio.ac.jp; e-Mail: nisiyama@chem.keio.ac.jp;
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Publikationsverlauf

Received 28 August 2001
Publikationsdatum:
05. Februar 2007 (online)

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Abstract

The anodic oxidation of phenol derivatives generates radical and cationic species, which upon coupling with other radicals, nucleophiles, and dienophiles provide a variety of bioactive natural products. The reaction conditions are controlled by electric potentials, solvents, supporting salts, electrodes, and so on to obtain the desired products. Both single- and two-electron reactions have been studied. The application of these reactions towards the synthesis of several target molecules will be discussed here.

1 Introduction

2 Single-electron Oxidation

2.1 Radical Coupling to C-C and C-O Bonds

2.2 Phenolic Oxidation of Bromophenols Towards Bioactive
Natural Products

3 Two-electron Oxidation

3.1 Cationic Reaction

3.2 [4+2] Cycloaddition

3.3 [3+2] Cycloaddition

3.4 [5+2] Cycloaddition

3.5 Intramolecular [5+2] Cycloaddition

4 Conclusion

Key words

anodic oxidation - bioactive natural products - single-electron oxidation - two-electron oxidation