The Untold Journey of Total Synthesis of Natural Products

Abstract This personal Account presents the developments of two synthetic strategies (Phenol Oxidative Dearomatization, POD; and Furan Oxidative dearomatization, FOD) for total synthesis of natural products. The POD program was originally derived from our first total synthesis of tenuipyrone, while our productive FOD program arose from the total synthesis of the uprolide family. Instead of a review summary of our total synthesis, this Account is focused on how these total synthesis projects are conceived and connected from the perspective of laboratory development. It is evident that total synthesis is not an isolated event, but a connecting and inspirational point that sparks new ideas and new projects. 1 Introduction 2 Total Synthesis versus Synthetic Methodology 3 Development of Phenol Oxidative Dearomatization (POD) for Total Synthesis 4 Development of Furan Oxidative Dearomatization (FOD, Achmatowicz rearrangement) for Total Synthesis 5 Conclusion and Outlook