Intro and Occurrence

TLDR
  • Natural Occurrence and Applications: Ethers and epoxides are common in nature, with examples like brevenal (studied for Cystic Fibrosis treatment) and disparlure (a gypsy moth pheromone used in pest control).
  • Synthetic Utility: Ethers are stable solvents ideal for reactions with reactive species, while epoxides are versatile intermediates used to create functionalized alcohols, chiral molecules, and pharmaceuticals.

Epoxides and ethers are common in nature.  Some important and interesting natural ethers include palytoxin (isolated from marine corral),  brevisamide, and brevenal (both isolated from marine plankton).  Brevenal is currently under study as a treatment for Cystic Fibrosis.

An important naturally occurring epoxide is disparlure.  Disparlure is a sex pheromone of gypsy moths attracting male gypsy moths.  Gypsy moth wreak havoc on certain crops.  One method to battle this is to combine disparlure with an insecticide.  The gypsy moths are attracted to the disparlure and are concomitantly poisoned with the insecticide.

Beyond their natural occurrences, ethers and epoxides are invaluable in organic synthesis. Ethers often serve as excellent solvents due to their stability and low reactivity, making them ideal for facilitating many reactions, including those involving highly reactive species such as Grignard reagents. Epoxides on the otherhand are highly versatile intermediates in organic chemistry due to their strained three-membered ring structure, which makes them highly reactive toward nucleophiles. This reactivity allows chemists to open the epoxide ring in a controlled manner, generating a wide variety of functionalized alcohols or other compounds. For example, epoxides are commonly used in the synthesis of pharmaceuticals, agrochemicals, and polymers. The ability to selectively open epoxide rings in the presence of different reagents has made them a cornerstone of asymmetric synthesis, enabling the construction of complex, chiral molecules with precision.