Investigations Of Acetylenic Selenide Of Hydroarylation And Synthesis Of Racemic Oseltamivir

Shikimic acid is an attractive chiral synthon with is hightly functionalized, six membered carbocyclic ring and multiple asymmetric centers. Shikimic acid is obtained via tedious isolation procedures from plants,unfortunately, current isolation of shikimic acid from the fruit of lllicium precludes its use in synthesis. Therefore, it would be desirable to provide a method to produce large quantities of shikimic acid. A short and practical synthesis of oseltamivir was accomplished is4steps from inexpensive and commercial crotonaldehyde strating material in our laboratory.Oseltamivir phosphate is the prodrug of the potent neuraminidase inhibitor and targeted for use as an orally active anitiral compound for prevetion and treatment of influenza infections. The current manufacturing process for oseltamivir starts from (-)-Shikimic acid or (-)-quinic acid, but the limited availability of the chiral raw materials is a major drawback. On the basis of the discovery synthesis, a short and practical synthesis of oseltamivir was accomplished in6steps from inexpensive and commercial3-Pentyl formate strating material in our laboratory, which provided an economical and practial alternative for the synthesis of oseltamivir.The prevalence of functionalized alkenes as synthons for the elaboration of multisubstituted alkenes renders them one of the most important building blocks in organic chemistry. Alkynyl selenides play an important role in organic synthesis by serving as crucial synthons in the transformations of a wide range of functional groups with a high degree of selectivity Alkynyl selenides can be transformed into substituted olefins by hydrohalogenation, hydrozirconation, hydroarylation.