Document Type
Article
Publication Date
2024
DOI
10.1039/D4QO00380B
Publication Title
Organic Chemistry Frontiers
Volume
11
Issue
13
Pages
3729-3776
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.
Rights
© 2024 The Authors.
This article is licensed under a Creative Commons Attribution 3.0 Unported (CC BY 3.0) License.
Original Publication Citation
Pote, A. R., Weierbach, S. M., Peczuh, M., & Lambert, K. M. (2024). Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products. Organic Chemistry Frontiers,11(13), 3729-3776. https://doi.org/10.1039/D4QO00380B
ORCID
0000-0002-0963-200X (Weierbach), 0000-0002-8230-2840 (Lambert)
Repository Citation
Pote, Aditya R.; Weierbach, Shayne M.; Peczuh, Mark W.; and Lambert, Kyle M., "Advancements in the Synthesis of Polyoxygenated Oxepanes and Thiepanes for Applications to Natural Products" (2024). Chemistry & Biochemistry Faculty Publications. 294.
https://digitalcommons.odu.edu/chemistry_fac_pubs/294