Part I. Synthetic Investigations of Heterocyclic Natural and Unnatural Compounds: Part II. New Approach to Latent Fingerprint Detection on Paper

The didemnin family of marine depsipeptides, as well as the closely related tamandarin family, have been of great interest to the scientific community since their discovery in 1981. This five chapter dissertation presents and discusses depsipeptides and their therapeutic and practical uses, notably their use in latent fingerprint detection. Chapter 1 discusses the biological and synthetic significance of the didemnins, tamandarins, and related natural products. Chapter 2 presents improved second-generation synthesis of the tamandarin B macrocycle and its successful application to the syntheses of three novel tamandarin B analogues. The results of these investigations help explain the structure-activity relationship, as well as mode of action, of these natural products. Chapter 3 deals with the generation of structurally intriguing azabicyclic and aminocyclopropanes, and their application in ring-opening conditions beneficial to pharmaceutical motifs. Chapter 4 introduces a rapidly growing family of natural diketopiperazine alkaloids: epipolythiodiketopiperazine (ETP) alkaloids, and related synthetic efforts in the generation of these alkaloids. Extensive synthetic investigation towards the formal synthesis of epicoccin G and other related alkaloids have been conducted. A novel methodology to access the framework present in many ETP alkaloids is discussed. Chapter 5 deals with the development and successful application of 1,2-indanedione functionalized gold nanoparticles in a modified multi-metal deposition process for the development of latent fingerprints on paper. Although a wide variety of ninhydrin-like compounds have been developed as chemical agents for this process over the years, considerable portions of latent fingerprints still escape detection. The new approach provides an alternative method of fingerprint detection that could be utilized in challenging situations.