Synthesis of alpha-Oxygenated Carbonyl Compounds via Dioxygenation, Development of Fluorescent Probes.

摘要

This thesis is divided into two parts. Part I consists of two chapters which describe a new dioxygenation reaction of alkenyl boronic acids to access alpha-hydroxy ketones. The methodology for a diastereoselective dioxygenation has also been reported. Part II also has two chapters which illustrate the importance of protein-lipid interactions and the development of environmentally sensitive fluorescent probes for monitoring these interactions.;In chapter 1, the Chan-Lam coupling of boronic acids and methods to synthesize alpha-hydroxy ketones are briefly reviewed. This is followed by a study on the optimization and the scope of the coupling reaction of alkenyl boronic acids with Nhydroxyphthalimide, rearrangement of the ensuing N-enoxyphathlimides and hydrolysis to release the alpha-oxygenated ketones. Chapter 2 reviews methods to control diastereoselectivity in a [3,3] rearrangement and the use of N-hydroxyisoindolinones to control the diastereoselectivity during the dioxygenation process.;Chapter 3 describes the fundamentals of lipids, their interactions with proteins and demonstrates that the use of environmentally sensitive probes is the most desirable method for monitoring these interactions. Chapter 4 exemplifies the development of new environmentally sensitive, thiol reactive probes which can be used for the in-situ determination of phosphatidylserine in the E. coli cell.