Efficient Syntheses of Natural Products and Target Molecules

Abstract

In the modern era of organic chemistry, short total syntheses that produce synthetically useful quantities of difficult to access natural products are championed. Natural product total synthesis is strongly supported through: (a) the development of new synthetic methodologies; (b) the exploration of novel chemical structures; and (c) investigation of compound reactivity. This thesis, submitted in publication format, describes the importance associated with the development of practical, short and scalable syntheses of natural products and target molecules. Described herein is the shortest total synthesis of natural product selaginpulvin D, the first genral synthesis of 2,3-diethynyl-1,3-butadienes, the first synthesis of a family of five novel TEE (tetraethynylethylene)/TVE (tetravinylethylene) hybrids and the first synthesis of a family of dendra-allenes. The importance of development of new synthetic methodology and the ability to access and explore the reactivity associated with fundamental hydrocarbons will be highlighted throughout.