Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Anthony G. M. Barrett; Tsz-Kan Ma; Thomas Mies

doi:10.1055/s-0037-1610382

Synthesis, Table of Contents

CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 67-82
DOI: 10.1055/s-0037-1610382

short review

Copyright with the author

Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Anthony G. M. Barrett *

Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London, W12 0BZ, UK Email: agmb@ic.ac.uk

,

Tsz-Kan Ma

,

Thomas Mies

› Author Affiliations

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.

1 Introduction

2 Cationic Polyene Cyclizations

2.1 Lewis Acid Mediated Polyene Cyclizations

2.2 Brønsted Acid Mediated Polyene Cyclizations

2.3 Halogen Electrophile Initiated Polyene Cyclizations

2.4 Sulfur Electrophile Initiated Polyene Cyclizations

2.5 Transition-Metal-Mediated Cationic Polyene Cyclizations

3 Radical Polyene Cyclizations

3.1 Transition-Metal-Mediated Radical Polyene Cyclizations

3.2 Photocatalyst-Mediated Polyene Cyclizations

4 Origin of Stereocontrol in Polyene Cyclizations

5 Conclusion

Key words

polyene cyclization - cascade reaction - carbon–carbon bond formation - natural products - total synthesis

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