Abstract
Abstract Inositol phosphates and the pathways that create them are ubiquitous means by which cells respond to extracellular stimuli and transmission of signals across cell membranes. Systematic biological study of these signaling pathways requires a good supply of phosphoinositol derivatives and their enantiomers. Development of efficient synthetic routes to isomeric inositols and their derivatives is thus, the most practical way to obtain such compounds on a considerable scale. This thesis describes the regioselective acylation of myo-inositol, its desymmetrization using asymmetric acylation and its application in the synthesis of nine optically active inositol phosphates. Chapter 1 provides a general introduction to inositol, its nomenclature, and biological significance. Chapter 2 introduces the inositol phosphates. The metabolism of inositol phosphates and their involvement in cell-cell signaling pathways is also discussed. A brief insight on the general synthetic considerations and literature reports for the synthesis of various inositol phosphates and its derivatives is provided in Chapter 3. Chapter 4 illustrates the specific aims and development of new synthetic strategy for the regioselective acylation and one-pot protection of myo-inositol. The desymmetrization of myo-inositol using various chiral auxiliaries is also described. Chapter 5 is dedicated to the efficient synthesis of various optically active inositol phosphates starting from a common chiral intermediate. A brief conclusion drawn from the synthetic work is given in Chapter 6. Finally, Chapter 7 provides the detailed experimental procedures and the physical data of the compounds synthesized for this dissertation.