Synthetic Studies of Madeirolide A: Visible-Light-Induced Radical Cyclization Approach

Abstract

In this thesis, our synthetic efforts toward marine natural product mardeirolide A are described. Madeirolide A is a biologically active polyketide that belongs to a group of macrolides. Madeirolide A have three bicyclic ether units embedded within a stereochemically decorated macrolactone scaffold. The bioactivity and structural complexity make madeirolide A an attractive target for total synthesis. Our approach for the synthesis of madeirolide A is based on the assembly of four fragments – C1-C10 fragment (A ring), C13-C19 fragment (B ring), C20-C27 fragment (C ring), and cinerulose fragment. Constructions of three oxacycles have been carried out through radical cyclization using a visible-light-induced transformation rapidly developed area in the past decade. Chapter 1 contains the background about madeirolide A, biological activity and structure features. Also, presented briefly are all published synthetic studies. Chapter 2 discusses all of the efforts that have been carried out in the laboratory towards a total synthesis of madeirolde A.