The body of this thesis comprises three main chapters and a final chapter for a summary and conclusions of the research.

Chapter one is a brief introduction to Achmatowicz rearrangement, a chemical transformation that has served as a key reaction for the construction of the principal intermediates in the present research work. The chapter includes some relevant examples of transformations of Achmatowicz rearrangement products, as well as significant recent applications of it in the total synthesis of natural products developed in our research group.

In Chapter two, it is described the asymmetric total synthesis and the verification of the antibacterial activity of two compounds belonging to a group of marine natural products called siladenoserinols, isolated in 2013. Siladenoserinols A...[ Read more ]

The body of this thesis comprises three main chapters and a final chapter for a summary and conclusions of the research.

Chapter one is a brief introduction to Achmatowicz rearrangement, a chemical transformation that has served as a key reaction for the construction of the principal intermediates in the present research work. The chapter includes some relevant examples of transformations of Achmatowicz rearrangement products, as well as significant recent applications of it in the total synthesis of natural products developed in our research group.

In Chapter two, it is described the asymmetric total synthesis and the verification of the antibacterial activity of two compounds belonging to a group of marine natural products called siladenoserinols, isolated in 2013. Siladenoserinols A and H were found to show moderate inhibitory activity toward the p53-Hdm2 interaction, which is a very attractive target for the development of new anticancer drugs. The synthetic strategy features an Achmatowicz rearrangement for the preparation of the bicyclic 6,8-DOBCO core, as well as two different olefination methods (Horner-Wadsworth-Emmons and Julia-Kocienski) for the incorporation of the side chains in a convergent manner. The total synthesis of these compounds allowed us to further examine their bioactivities in a panel of cancer lines and bacterial cells.

In Chapter three, we describe the synthetic studies towards a group of natural products of the meroterpenoid family called, the berkeleyacetals, which are structurally complex natural products that have shown potent anti-inflammatory activity in various biological essays published by many scientists. The biological activity of these kind of compounds is of wide interest due to its promising pharmacological potential. The presence of a highly dense oxygen functionality and a polycyclic ring system in berkeleyactetals pose significant synthetic challenges. In this chapter, it is reported an efficient strategy for the construction of the tetracyclic core system of berkeleyacetal. The synthetic strategy features two cycloadditions ([4+2] and [5+2]) to forge the tetracyclic core and Achmatowicz rearrangement for the preparation of the cyclization substrates containing B and E rings found in the core structure of berkeleyacetals.

The main experimental procedures, the characterization data of major compounds, including XRD characterization data, and the cited references are found at the end of chapters two and three of this thesis. Copies of the original ¹H and ¹³C NMR spectra of key compounds are given in the Appendix.