ABSTRACT Oxanorbornyl adducts derived from the Diels-Alder reactions of furan and various dienophiles have been used extensively by chemists in the synthesis of cyclohexyl moieties of a wide array of organic compounds. We, for example have extensively used the Diels-Alder adducts of furan and the dienophiles ethyl (E)-nitroacrylate and maleic anhydride in the synthesis of a wide array of hydroxycyclohexyl β-amino acids. Three methods have been delineated for the elaboration of the oxanorbornyl adducts to the cyclohexyl systems. These are base mediated fragmentation, acid mediated fragmentation and transition metal-catalysed ring-opening reactions. This article presents a systematic and critical review of the work by our group and by others towards the use of oxanorbornyl adducts of furan and various dienophiles in the synthesis of cyclohexyl systems.
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