Abstract
Saturated oxygen heterocycles are widely found in a broad array of natural products and other biologically active molecules. In medicinal chemistry, small and medium rings are also important synthetic intermediates since they can undergo ring-opening and -expansion reactions. These applications have driven numerous studies on the synthesis of oxygen-containing heterocycles and considerable effort has been devoted toward the development of methods for the construction of saturated oxygen heterocycles. This paper provides an overview of the biological roles and synthetic strategies of saturated cyclic ethers, covering some of the most studied and newly discovered related natural products in recent years. This paper also reports several promising and newly developed synthetic methods, emphasizing 3–7 membered rings.
Highlights
Constituting more than half of all the known organic compounds, heterocyclic compounds play an important role in organic chemistry
A large number of natural products containing cyclic ethers have a wide range of interesting biological activities
Given that most natural products occur as single enantiomers, and that chiral drugs on the market are regulated to be single enantiomers, special attention has been devoted to the asymmetric synthesis of heterocyclic compounds, as they play fundamental biological roles
Summary
Constituting more than half of all the known organic compounds, heterocyclic compounds play an important role in organic chemistry. Among these, saturated cyclic ethers are abundant, appearing in a large number of biologically active natural products and pharmaceutically active compounds. The many FDA-approved cyclic ether rings containing therapeutic compounds (Figure 1) suggest and are evidence that cyclic ethers are significant motifs during the development of potential drug molecules. They have been frequently found as key structural units in synthetic pharmaceuticals and agrochemicals. Given that most natural products occur as single enantiomers, and that chiral drugs on the market are regulated to be single enantiomers, special attention has been devoted to the asymmetric synthesis of heterocyclic compounds, as they play fundamental biological roles.
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