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CC BY-NC-ND 4.0 · Synthesis 2021; 53(22): 4187-4202
DOI: 10.1055/s-0037-1610776
special topic
Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products

Kevin Rafael Sokol
,
Thomas Magauer  ∗
T.M. acknowledges the European Research Council under the European Union’s Horizon 2020 research and innovation program (grant agreement No. 714049) and the Center for Molecular Biosciences (CMBI).
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Abstract

The construction of oxepin and dihydrooxepin containing natural products represents a challenging task in total synthesis. In the last decades, a variety of synthetic methods have been reported for the installation of these structural motifs. Herein, we provide an overview of synthetic methods and strategies to construct these motifs in the context of natural product synthesis and highlight the key steps of each example.

1 Introduction

2 Oxepin Natural Products

3 Dihydrooxepin Natural Products

3 Brønsted or Lewis acid Catalyzed Cyclization

3.2 Radical Cyclization

3.3 Substitution and Addition Cyclization

3.4 Sigmatropic Rearrangement

3.5 Oxidative Methods

3.6 Transition Metal Catalyzed Cyclization

4 Summary

Key words

oxepin - dihydrooxepin - natural product - total synthesis - heterocycles


Publication History

Received: 15 April 2021

Accepted after revision: 25 May 2021

Article published online:
24 June 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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