Chapter 1 provides an introduction to the metabolism of aromatic compounds by enzymes, and the use of bioproducts in synthesis. A brief introduction into the synthesis and potential applications of amino alcohols is also discussed. Finally, a summary of a number of methods for the-determination of enantiomeric excess concludes the chapter. Chapter 2 investigates the synthesis oftrans-dihydrodiols from their cis-dihydrodiol precursors. The desymmetrisation ofmeso-l,2-dihydroxycyclohexane is also discussed. The chemoenzymatic synthesis oftrans-I,2-aminocyclohexanols, including the biologically important compound vesamicol is examined. Chapter 3 explores the synthesis of a number ofcis- and trans-azido alcohols from bromo- and chIoro- benzene, and the conversion ofthe azido alcohols to cis- and trans-amino alcohols. A brief investigation into the substitution ofthe halide atom in bromobenzene-cis-diol is discussed as a potential route to a library ofcis- and (rmlS- amino alcohols. Chapter 4 is divided into three parts. The first section discusses a number of synthetic routes to vicinal cis- and trmls- amino alcohol derivatives of naphthalene. The second section outlines the bacterial metabolism ofselected polycyclic aromatic hydrocarbons and the formation of bis-cis-diols. The final section introduces a new class of bacterial metabolites from acetonide-protected diol substrates.