Bisphosphonates for modified nucleotide synthesis and related chemistry

This dissertation explores the field of organophosphorus chemistry. Phosphorus plays a major role in medicinal and natural product chemistry, which is the inspiration for the majority of the work presented in this dissertation.;The first chapter is a short description of the vast field of organophosphorus chemistry. Phosphorus holds a unique place in the periodic table and its wide spread applications in various fields are presented. Short descriptions of the most important applications are explored, with special emphasis on phosphorus based reagents and biological relevant molecules.;Chapter 2 describes the one pot synthesis of Kabachnik-Fields reaction for fluorinated alpha-aminophosphosphonates, amino acid analogs, with gallium triflate. Some mechanistic aspects are explored with respect to fluorinated imines and aminals.;Chapter 3 deals with various pyrophosphonic acid analogs of bisphosphonic acids,triphosphate analogs. The pKa's of 3,3,3-trifluoro-2,2-dihydroxypropylphosphonic acid, a pyrophosphonic acid analog are evaluated. The synthesis of modified nucleotide analog with 3,3,3-trifluoro-2,2-dihydroxypropylphosphonic acid is described.;Chapter 4 presents a simple and mild reagent for the alpha-chlorination and alpha-bromination of ketones with acidic alpha-hydrogens. TMS-X (where X= Br, or Cl) and KNO3 salt is used to carry out alpha-bromination and alpha-chlorination with good conversion and selectivity.