Cyclitols: Conduritols and Related Compounds

M.   Serdar   Gultekin; Murat      Celik; Metin      Balci

doi:10.2174/1385272043370069

Abstract

Conduritols are 1,2,3,4-cyclohexenetetrol isomers and exist in ten possible isomeric forms (two mesofour DL-pairs) and have been labelled A, B, C, D, E and F. All of the possible conduritol isomers have already been synthesised starting from completely different materials and their biological importance studied. Transformation of the aromatic compounds into diols has opened up a new synthetic approach to the various conduritol isomers and their derivatives. Conduritols are useful precursors in the preparation of cyclitols such as myo-inositols phosphates and pseudo-sugars, some of which are important mediators in many cellular processes. Conduritol epoxides and aminoconduritols act as inhibitors of glycosidases, cyclophellitols have proven to be potent inhibitors of human immunodeficiency virus (HIV) and glycosidases and conduritol-A analogues modulate the release of insulin. This review is not intended to be exhaustive and is aimed at highlighting the progress in the synthesis of conduritols and their derivatives, as well as their synthetic applications and biological importance mainly in the last decade.

Keywords: cyclitols, conduritols, cyclohexenetetrol isomers, conduritol epoxides, aminoconduritols, glycosidases