Preparation and synthetic applications of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives

Abstract

The development of efficient routes to multi-gram quantities of chiral synthons is a key issue in the total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en3- one template is an appealing starting material for the development of non-iterative approaches to polyoxygenated fragments that are found in a large variety of biologically relevant natural compounds. Desymmetrization and resolution procedures, stereoselective functionalizations and double-chain elongations represent attractive strategies for such synthetic challenges. © Schweizerische Chemische Gesellschaft.