STUDIES ON THE ROLE OF CONFORMATION AND OF HYDROGEN-BONDING ON THE DIHYDROXYLATION OF CYCLIC ALLYLIC ALCOHOLS - APPLICATION TO THE SYNTHESIS OF CONDURITOL-D

A study on the dihydroxylation of a series of conformationally 'locked ' cyclohexenols is reported, The orientation of the hydroxy group (i.e . equatorial or axial) is crucial in determining the degree of diaster eoselectivity observed during oxidation, In some cases, the use of hyd rogen-bonding enables the stereoselective synthesis of syn triols and tetraols, This effect has been utilised in the synthesis of conduritol D: X-ray crystal structure analysis provided a method of assigning th e relative and absolute stereochemistry of an advanced synthetic inter mediate.