Studies involving potassium permanganate mediated oxidative cyclisations of 1, 5-dienes and 1, 5, 9-trienes.

The use of potassium permanganate to oxidatively cyclise 1,5-dienes has been well documented, albeit with disappointing yields. The aim of this study has been to optimise the reaction conditions for the oxidative cyclisation of a commercially available 1,5-diene using potassium permanganate. The optimised methodology has then been applied to a selection of readily accessible isomeric 1,5,9-trienes in order to give tetrahydrofuran lactol products with differing stereochemistry. The subsequent cleavage of the lactol products to lactones has been achieved producing four diastereoisomeric cz6'-2,5-disubstituted tetrahydrofurans in order to access potential precursors to natural molecules. biologically active and unnatural