Synthesis of D-Pinitol and L-Pinitol via a new method

In recent years, using natural bioactive compounds in food supplements and drug ingredients have been more preferred in order to reduce or prevent side effects. Hence, the total synthesis of bioactive natural products and their derivatives have drawn great attention from many researchers. D-Pinitol, a natural molecule, involves in many biological processes besides shows antioxidant, anti-inflammatory, anticancer and antidiabetic properties. In addition, scientists working in fields such as pharmaceutical chemistry, chemistry and medicine sustain to examine D-Pinitol, which is considered as a potential preventive agent for diabetes and many diabetes-related diseases and is a crucial precursor in the synthesis of bioactive molecules. Considering all these aspects, research on the development of new methods for the synthesis of D-Pinitol and its enantiomer L-Pinitol which is used in biological evaluations, has become crucially important. In this dissertation, to afford D-pinitol and L-pinitol a new asymmetric method which can be an alternative to methods known in the literature has been developed. In the key step of this method, Pd- catalyzed dynamic kinetic resolution reaction of racemic conduritol B derivative was utilized to obtain enantiomers of conduritol B derivatives. This synthetic route proceeds through the inversions of the two allylic groups of conduritol B derivatives to provide enantiomerically pure forms of conduritol E derivatives. The synthesis of D- and L-Pinitol was carried out stereoselectively by epoxidation of conduritol E enantiomers followed by ring opening of conduritol E oxiranes in stereo- and regioselective manners. In conclusion, this total synthesis to obtain D-Pinitol and L-Pinitol provides a novel approach using commercially available, inexpensive and achiral p-benzoquinone as the starting material.