An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

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.

In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against Monilinia fructicola

“…It is expected that the discovery of these molecules will be a precedent for the development of new molecules modifications mainly on the exocyclic double bond of the natural ketone, which would further enhance its antifungal effect [33][34][35]. Our findings show that compounds 7 and 8 are capable of combating highly resistant strains such as strain 1 at higher concentrations, which would allow combating more aggressive strains that cause severe crop damage at flowering time.…”

Visible Light‐Induced Intramolecular C─O Bond Formation via 1,5‐Hydrogen Atom Transfer Strategy

“…Cyclic ethers are a valuable framework that is discovered in a wide range of naturally occurring compounds and bio‐active molecules 1–6 . Given the importance of these building blocks, a number of synthetic methods have been extensively developed.…”

“…Cyclic ethers are a valuable framework that is discovered in a wide range of naturally occurring compounds and bioactive molecules. [1][2][3][4][5][6] Given the importance of these building blocks, a number of synthetic methods have been extensively developed. Despite the broad applications of intramolecular C─O bond formation to obtain cyclic ether derivatives, many reactions often require high loading of transition metal catalysts or harsh reaction conditions such as high temperature.…”

Easily accessible non-aromatic heterocycles with handles: 4-bromo-2,3-dihydrofurans from 1,2-dibromohomoallylic alcohols

“…Non-aromatic heterocycles are ubiquitous in nature and widely targeted in synthetic methodology development. 1,2 While the ability to diversify aromatic heterocycles has exploded with the development of a range of cross coupling methodologies exploiting aromatic heterocycles with reactive handles, [3][4][5][6][7][8] ready access to non-aromatic heterocycles with such handles is lacking. We have been interested in functionalized non-aromatic heterocycles that can be used as templates for diversication.…”