Reactivity of (–)-Shikimic Acid as the Basis of Its Biological Role and a Template for the Development of Antiviral Agents: a Case Study of Oseltamivir Phosphate

The review is dedicated to the analysis of the current data in the field of molecular organization of unsaturated cyclic systems, using the example of the monocarboxylic unsaturated cyclic structure of (–)-shikimic acid, which exhibits the properties of both a carboxylic acid and a polyatomic vicinal alcohol, as well as cycloolefins, considering the influence of side substituents. The question of the most optimal method for the production of shikimic acid and its derivatives with a significant yield remains unresolved. The search for new synthetic routes and the potential use of compounds whose behavior follows the principles of the Diels-Alder/Alder-Stein reactions should be primarily determined by the peculiarities of their molecular organization. The study of the static system underlying the chemical structure of this acid, its reactivity, and the comparative analysis of possible methods and approaches for obtaining cycloalkenes with heteroatoms in the molecule, electron-accepting side groups using the example of the antiviral drug (oseltamivir phosphate), allowed for the investigation of the relationship between the properties and the structural parameters of this chemical object at a new qualitative and quantitative level. The conclusions drawn are, in our opinion, of great importance for understanding the factors that determine the behavior of reacting particles in the classical pair of diene/dienophile in a reaction mixture. Also discussed are methods for synthesizing artificial (–)-shikimic acid (hereafter referred to as “acid”) as a replacement for its costly extraction from plant raw materials, as well as the features of using this acid and similar compounds for the development of new pharmaceuticals.