Chapter 4 - Aryne-mediated construction of fluorene skeletons and its applications to total synthesis of selaginpulvilins

Abstract

The hexadehydro Diels–Alder (HDDA) reaction has recently emerged as a powerful tool for aryne formation, thereby giving access to highly functionalized aromatic skeletons. In this chapter, we describe an HDDA-based approach to the total synthesis of selaginpulvilins C and D, which relies on generation of an aryne intermediate in situ. The isolation, structural elucidation and biological activities of selaginpulvilins as well as other related alkynyl phenols are discussed, and various synthetic approaches to total synthesis of these natural products are reviewed.