2011 Theses Doctoral

Studies towards Selective Synthesis of Resveratrol-based Oligomeric Natural Products

Lin, Yunqing

Chapter 1. Recent synthetic approaches towards the resveratrol family of oligomeric natural Products This chapter outlines some of the past and present efforts in the field of resveratrol-based oligomeric natural product synthesis. Both biosynthetic approaches and stepwise synthetic approaches are discussed to present the current level of understanding regarding the controlled synthesis of these molecules in order to place the studies described in chapter 2 and 3 in better context. Chapter 2. Development of a general synthetic method towards different dimeric structures of the resveratrol family We have developed a general approach to achieve selective synthesis of the major dimeric architectures within the resveratrol family with the use of a unique key common intermediate possessing three aryl rings. Syntheses of three subclasses of resveratrol dimeric structures are reported. Chapter 3. Synthetic efforts towards dihydrobenzofuran-containing higher order resveratrol oligomers Finally, this chapter describes our current studies towards more complex members of the resveratrol family. A concise approach for dihydrobenzofuran ring installation on the sevenmembered carbon framework of resveratrol-based oligomers is reported. The formation of 7,5- fused ring natural product cores via Friedel- Crafts cyclizations provides controlled access to some of the highly complex architectures within the resveratrol family.