Oxetanes: formation, reactivity and total syntheses of natural products
Peter Gabko, Martin Kalník, Maroš Bella
TL;DR
This paper reviews the synthesis, reactivity, and use of oxetanes in creating natural products, focusing on recent developments since 2015.
Contribution
The paper provides an updated and comprehensive review of oxetane chemistry, including new synthetic methods and applications.
Findings
Various synthetic strategies for oxetane formation are reviewed, including de novo ring constructions.
Oxetanes show useful reactivity in ring-opening and ring-expansion reactions for natural product synthesis.
Recent total syntheses of oxetane-containing natural products are highlighted.
Abstract
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.
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Taxonomy
TopicsSynthesis and Catalytic Reactions · Synthetic Organic Chemistry Methods · Asymmetric Synthesis and Catalysis