New synthetic approaches to 8,5'-neolignans [Elektronische Ressource] / von Ljubisa Jovanovic

Institut für Chemie Arbeitsgruppe Prof. Peter NEW SYNTHETIC APPROACHES TO 8,5’-NEOLIGNANS Dissertation zur Erlangung des akademischen Grades "doctor rerum naturalium" (Dr. rer. nat.) in der Wissenschaftsdisziplin Organische Chemie eingereicht an der Mathematisch-Naturwissenschaftlichen Fakultät der Universität Potsdam von Ljubisa Jovanovic Potsdam, Juni 2005 TABLE OF CONTENTS TABLE OF CONTENTS AKNOWLEDGEMENTS LIST OF ABREVIATIONS CHAPTER 1: INTRODUCTION……………………………………………….….. 1 1.1 PHENOLICS……………………………………………………………………………….…....2 1.2 LIGNANS AND NEOLIGNANS…………………………………………………………….…3 1.3 DIHYDROBENZOFURANS AS A PART OF A COMPLEX MOLECULE……………….…5 1.4 SYNTHESIS OF NEOLIGNANS……………………………………………………………....7 1.4.1 BIOSYNTHESIS OF PHENYLPROPANOIDS………………………………………….….7 1.4.2 BIOSYNTHESIS OF NEOLIGNANS………………………………….8 1.4.3 CHEMICAL SYNTHESES OF NEOLIGNANS…………………………………………...10 1.4.3.1 The synthesis of dihydrobenzofuran compounds via directed α-metalation………………………………………………………………...19 1.4.3.1.1 Some possible side reactions in the preparation of phosphamidates…......25 CHAPTER 2: AIM OF THE WORK…………………………………………..…………30 CHAPTER 3: RESULTS……………………………………………………………... 31 3.1 NEW SYNTHETIC APPROACHES TO DIHYDROBENZOFURAN COMPOUNDS….…...31 3.1.1 DIRECTED α-METALATION APPROACH…………………………………………..….