Document Type
Article
Publication Date
2024
DOI
10.1039/D4QO00380B
Publication Title
Organic Chemistry Frontiers
Volume
Article in Press
Pages
48 pp.
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. Advance online publication. 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