2-Pyrone is extremely prevalent in numerous natural products with a broad range of biological activities. Not only structurally complex natural products, but more and more 2-pyrone containing small molecules have also attracted the attention of organic chemists, medicinal chemists and agricultural scientist. Synthesizing valuable 2-pyrone containing products and testing their potential applications are of great importance.

In this dissertation, we summarized the synthesis of two 2-pyrone containing small molecule natural products and explored methods to functionalize triacetic acid lactone, a very promising 2-pyrone compound that has been identified as a bio-privileged molecule. Chapter 1 of this dissertation describes the synthesis of a class of 6-alkyl-2-pyrones and an antileukemic 2-pyrone. Chapter 2 discusses the involvement of triacetic acid lactone in multi-component reaction. The versatility of the bio-based triacetic acid lactone as a platform chemical has been further demonstrated via the 3-component Mannich reaction. The last chapter describes an approach to Hibiscone C, a bioactive and structurally interesting natural product. A strategically new approach to this molecule was depicted.