Synthesis of Biaryl-Containing Medium-Ring Systems by Organocuprate Oxidation: Applications in the Total Synthesis of Ellagitannin Natural Products

摘要

In this feature article we discuss the construction of biar-yl-containing medium-sized rings by organocuprate oxidation and the application of this chemistry in the synthesis of members of the ellagitannin family of natural products. A concise and efficient total synthesis of the ellagitannin sanguiin H-5 is highlighted. Studies towards the synthesis of elaeocarpusin are also presented. 1.Introduction 2.Results and Discussion 2.1.Total Synthesis of Sanguiin H-5 2.2.Studies towards the Total Synthesis of Elaeocarpusin 2.2.1.Towards Elaeocarpusin: Organocuprate Oxidation 2.2.2.Towards Elaeocarpusin: A Double Esterification Approach 3.Conclusions