This dissertation consists of two parts. In the first part (Chapters I and II), thedevelopment of new molecular sensors for detection of asymmetry of organic moleculesis disclosed. These sensors, also referred to as “host molecules”, are capable of formingstable complexes with chiral organic molecules. The designs of the hosts are such thatthe point chirality of organic molecules is transferred into a helical twist of the molecularreceptor, leading to axial chirality which can be detected as Exciton Coupled CircularDichroism (ECCD). The absolute configuration of a few classes of organic molecules suchas chiral monoamines, cyanohydrins, sulfoxides, phosphine oxides, and mono alcoholsis assigned in a microscale, rapid and unambiguous manner.In the second part of this thesis (Chapters III and IV), the development of neworganic reactions and their further application towards the synthesis of natural productsis discussed. In Chapter III, the successful completion of the total synthesis of (–)-Salinosporamide A is described. During the synthesis of this molecule, new reactions aredeveloped that enabled the completion of this synthesis. In Chapter IV, the developmentof a halenium initiated spiroketalization and application of this methodology towards thetotal synthesis of Obtusin is disclosed. The enabling role of protecting group on thenucleophilic oxygen atom stands as a unique discovery that can improve the reactionoutcomes.
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