Carbohydrates to Carbocycles via Radical Aldehyde Cyclizations

Abstract

Previous work in this laboratory has shown that radical aldehyde cyclizations provide efficient routes for the preparation of cycloalkanols. This process seems well suited to carbohydrate substrates and could conceivably be developed for novel routes from carbohydrates to carbocycles. Several aldehydic substrates have been prepared with a variety of different radical progenitors. The preliminary conclusions seem to be that α-oxygenated aldehydes are poor substrates, a probable reason being that the intermediate alkoxy radicals are prone to decomposition by β-scission. The formation of the radical intermediates has been demonstrated by trapping experiments with acrylonitrile.