Synthesis 2020; 52(19): 2781-2794
DOI: 10.1055/s-0040-1707154
short review
© Georg Thieme Verlag Stuttgart · New York

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Leander Geske
,
Eisuke Sato
,
Till Opatz
Department Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, 55128 Mainz, Germany   Email: opatz@uni-mainz.de
› Author Affiliations
Financial support by the Alexander von Humboldt-Stiftung in the form of a postdoctoral fellowship (Dr. Eiskue Sato) is gratefully acknowledged.
Further Information

Publication History

Received: 09 April 2020

Accepted after revision: 12 May 2020

Publication Date:
22 June 2020 (online)


Dedicated to the memory of Professor Jun-ichi Yoshida (1952–2019)

Abstract

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.

1 Introduction

2 Shono-Type Oxidation

3 C–N/N–N Bond Formation

4 Aryl–Alkene/Aryl–Aryl Coupling

5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes

6 Spirocycles

7 Miscellaneous Transformations

8 Future Prospects