The first stable cis-cyclohexanediol was isolated in 1968 following studies of the microbial oxidation of aromatic hydrocarbons by soil bacteria. Metabolism of halosubstituted benzenes with a mutant strain of Pseudonomas putida yielded products in which two hydroxyl groups were introduced completely regiospecifically across the 2,3 bond having cis relative stereochemistry, Scheme 1.

                                                            Scheme 1

Cis-dihydrodiols 2 naturally lend themselves as good chiral precursors and have been used in the synthesis of many natural products including inositols, conduritols, carbohydrates and pseudosugars.  We envisaged that developing a successful strategy for introduction of an aryl group at the halogenated position in 2 would provide a route into the core of alkaloids of the Amaryllidaceae family such as amabiline 3.

            The Suzuki cross-coupling reaction is currently under investigation and preliminary results indicate that it will provide a useful strategy for introduction of the aryl group.