This dissertation details work that is done in a variety of subdisciplines of organic chemistry and demonstrates the importance and broad application of organometallic reagents, synthetic methodology as well as total synthesis. This work is divided into three unique chapters that showcase the extensive and useful variety of these subdisciplines. The first chapter involves the use of organometallics and methodology to build on previous work that utilized C-H activation to form benzofuranone motifs. Intensive studies have been accomplished and new and important reactivity characteristics have been reported. Chapter two involves the planned total synthesis of cyanomaclurin. Stereoselective reactions and various new synthetic pathways were endeavored. Many synthetic routes are presented that allow for synthetic versatility. These routes contain new and exclusive pathways that could allow for potential synthetic paths when targeting future natural products. The final chapter involves the use of (2Z,3E)-α,ß’-ß,gamma-unsaturated ester to access a variety of substituted dienes through a stereoselective one-pot process. This chemistry is very efficient and synthetically useful given its good yield and the four reaction one-pot synthetic pathway.