From Marco Polo to chiral stannanes - radical chemistry for the new millennium

Abstract

Over the past few decades, free-radicals have emerged as important intermediates in a large cross-section of disciplines ranging from chemical synthesis to biology and medicine. Freeradicals are now understood to be important in oxidative processes affecting areas that include materials science, DNA damage and heart disease, and are involved in many enzyme -mediated transformations. Significantly, radicals can be harnessed to provide powerful imaging tools and novel synthetic methodology with application to natural products and other chemistries. This review describes the author's involvement in the development of new free-radical technology useful for the preparation of compounds of biological importance. Examples include the use of carbon-centred radicals to prepare selenium-containing compounds that are then used as freeradical scavengers and antioxidants. Novel reagents have been developed to perform enantioselective free-radical chemistry with the aim of preparing novel pharmaceuticals.Examples are provided.

Vitamin E models. Conformational analysis and stereochemistry of tetralin, chroman, thiochroman and selenochroman

“…It is in human nature to wonder if 'Mother Nature' did the best possible structural arrangement or whether we can improve upon it. The question has been asked [13,14] in general, about antioxidants and in particular about vitamin E [16,17].…”