Issue 13, 2024

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Abstract

Oxepanes are central motifs and tenants of many biologically important molecules, and their synthetic construction often presents a challenge to chemists due to consequential entropic and enthalpic barriers that have limited the synthetic toolbox to access these seven-membered oxacycles. This review covers the breadth of synthetic methods to afford the oxepane/thiepane moiety, with a focus on polyoxygenated oxepanes and includes radical cyclizations, Lewis acid-mediated cyclizations, ring closing-metathesis, Nicholas–Ferrier rearrangement, homologations, and ring-expansion strategies. Implementation of these tactics towards sugar-based and non-sugar based (de novo) approaches is presented alongside their extensive application to the total synthesis of several complex polyoxygenated oxepane-containing natural products, which are also highlighted.

Graphical abstract: Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Article information

Article type
Review Article
Submitted
28 Feb 2024
Accepted
09 May 2024
First published
10 May 2024
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 3729-3776

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

A. R. Pote, S. M. Weierbach, M. W. Peczuh and K. M. Lambert, Org. Chem. Front., 2024, 11, 3729 DOI: 10.1039/D4QO00380B

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