The quest for selenocycles: From an ESR spectrum to a commercial product

Selenium compounds have a checkered history. Originally considered to be highly toxic, the tide turned in the 20th century when selenium was discovered to be an essential trace element; indeed, selenium is the least abundant element on Earth to have a well-defined biological role. Despite this new-found importance, organoselenium compounds were largely curiosities because methods for their synthesis were cumbersome and unpleasant and often involved toxic reagents and/or hazardous procedures. This paper describes how work carried out in collaboration with Alwyn Davies in the late 1980s, aimed at acquiring Electron Spin Responance (ESR) spectra of selenophene radical anions and cations, led to the development of free-radical methods for the synthesis of numerous selenium-containing heterocycles, many of which showed interesting and useful biological properties. This journey ends with the development of selenium-containing carbohydrates (selenosugars) that exhibit unique skin-repair properties and the establishment of Seleno Therapeutics as a vehicle for the commercialization of these selenosugars.

Automated summary

Selenium compounds were initially considered toxic but later discovered to be essential trace elements. Despite their importance, the synthesis of organoselenium compounds was difficult and unpleasant. However, collaboration in the late 1980s led to the development of free-radical methods for synthesizing selenium-containing heterocycles with interesting biological properties.