Synthetic efforts toward the total synthesis of premnalatifolin A & monomeric unnatural icetexane analogs

Abstract

Icetexanes are a family of natural products with a wide array of biological activities and complex structure, which has encouraged synthesis chemists to approach them with different strategies over the past decade. Chapter 1 outlines the different types of icetexanes and then takes a closer look at the newly discovered icetexanes—since 2009—and their biological activities. Chapter 1 is then concluded with a discussion around the last decade of development on the synthesis of icetexane natural products and their core structure. ☐ Chapter 2 outlines the prior and current effort on synthesis of icetexanes and their core 6–7–6 structures. Inspired by the remarkable works of Mr. Daniel J. Moon and Dr. Mohammad Al–Amin in the Chain Laboratory, chapter 2 is focused on development of a small library of inverted icetexanes. During this chapter the capability of the Richie formylation in generating para methoxy benzaldehydes as well as a new tandem formylation–cyclization reaction to synthesize both dihydrobenzofurans and dihydrobenzopyrans was demonstrated. ☐ Chapter 3 focuses on the synthesis of conventional unnatural icetexane analogs. Additionally, chapter 3 outlines the path toward completion of premnalatifolin A’s monomers and in due course, the natural product premnalatifolin A itself.