Desymmetrization of Cyclohexa-1,4-dienes − A Straightforward Route to Cyclic and Acyclic Polyhydroxylated Systems

A straightforward route to polyols, amino polyols, polysubstituted lactols and lactones from readily available arenes has been devised. It uses a three- or four-step sequence involving a Birch reduction of the arene, followed by desymmetrization through dihydroxylation or aminohydroxylation and, lastly, ozonolysis of the remaining olefin. Depending on the ozonolysis workup conditions, cyclic or acylic synthons were obtained in generally high overall yields and with excellent levels of stereocontrol. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)