UC Irvine

The first part of this thesis illustrates the application of kinetic resolution reagents for the determination of absolute configuration. A dual-catalytic approach based on ion pair recognition was explored using the combined action of 4-(N,N-dimethylamino)pyridine (DMAP) and a chiral thiourea receptor co-catalyst. After difficulties were encountered with a dual-catalytic mode, an alternative approach using enantioselective acyl transfer reagents was investigated. The new strategy led to a successful development of a new and efficient method to rapidly establish the absolute configuration of primary amines using mass spectrometry. Part two of this thesis describes the development of a modular approach toward the synthesis of the Lycopodium alkaloids. A highly concise six-step total synthesis of the complex alkaloid (+)-fastigiatine was accomplished using a transannular Mannich reaction that generated two quaternary carbons at a late stage. The modular approach to fastigiatine will be expanded to other members of the family including himeradine A and lyconadin A.