Epoxide-Opening Cascades Triggered by a Nicholas Reaction; Total Synthesis of Teurilene

摘要

The way in which nature approaches the synthesis of complex molecules is a great source of inspiration to organic chemists for planning a synthetic route to a natural product. In this context, cascade cyclizations are considered a valuable tool for obtaining molecular complexity in a straightforward manner. Focusing on polycyclic ethers, it is well accepted by the scientific community that these types of compounds originate from a cascade cyclization of a polyepoxide backbone, thus leading to structures such as the ones depicted in Figure 1. Therefore, epoxide-opening cascades have been used as a valuable methodology to synthesize polycyclic ether natural products such as polyether ionophores as well as squalene-derived and ladder-type polyethers. Additionally, another valuable synthetic strategy is the bidirectional approach. Several groups have achieved the synthesis of many natural products using this concept.