Oxetanes: formation, reactivity and total syntheses of natural products

Oxetanes are 4-membered cyclic monoethers which have found important applications in medicinal chemistry as polar and metabolically stable isosteric replacements for gem-dimethyl and carbonyl groups. This work reviews possible synthetic strategies towards these strained heterocycles, covering both d...

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Bibliographic Details
Main Authors: Peter Gabko, Martin Kalník, Maroš Bella
Format: Article
Language:English
Published: Beilstein-Institut 2025-06-01
Series:Beilstein Journal of Organic Chemistry
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Online Access:https://doi.org/10.3762/bjoc.21.101
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Summary:Oxetanes are 4-membered cyclic monoethers which have found important applications in medicinal chemistry as polar and metabolically stable isosteric replacements for gem-dimethyl and carbonyl groups. This work reviews possible synthetic strategies towards these strained heterocycles, covering both de novo constructions of the 4-membered ring as well as derivatisations of oxetane building blocks, then reactivity of oxetanes in terms of ring-opening and ring-expansion reactions, and finally total syntheses of selected oxetane-containing natural products. The literature review primarily covers reports made after the year 2015, but a few older contributions that were considered relevant are also discussed.
ISSN:1860-5397