I. Platinum-catalyzed rearrangement of beta-keto-propargyl alcohols. II. Approaches toward the synthesis of lignan natural products. III. Direct arylation of heteroaromatics. IV. Hydrolysis of 2,6-dichloronicotinic acid. V. S-arachidonoyl-2-thioglycerol (

The development of new methods and strategies, as well as expanding mechanistic understanding at the molecular level remain important goals in synthetic organic chemistry. This work is a collection of five projects that aim to further organic chemistry through development in methods, strategies, and mechanistic understanding.;Chapter 1. A new Pt-catalyzed method to convert beta-keto-propargyl alcohols to 3(2H)-furanones has been described. An enedione byproduct formed under the reaction conditions for a subset of propargyl alcohols has been explored. A mechanism that accounts for the experimental observations has been proposed.;Chapter 2. Several approaches toward the synthesis of frameworks of lignan natural products have been outlined. These approaches have focused around the exploitation of symmetry as a strategy for the construction of lignan natural products. One strategy, based on a double direct arylation of furans and thiophenes has allowed the construction of dibenzylbutane lignan frameworks.;Chapter 3. The direct arylation of various electron-rich heterocycles to form mono- and bis-arylated frameworks was investigated. Extension of the direct arylation methodology to a sequential intermolecular decarboxylative palladation -- direct arylation was demonstrated.;Chapter 4. The base-promoted solvolysis of 2,6-dichloronicotinic acids has been investigated. A reversal in the distribution of products dependent on the countercation of the base has been described.;Chapter 5. The design and synthesis of a thioester probe for monoacylglyceride lipase (MAGL) was carried out. Starting from glycerol, 2-mercaptoglycerol was synthesized, and then arachidonoylated to make a thioester mimic of the endogenous cannabinoid ligand 2-arachidonoylglycerol.