Kaiser, M., Schönbauer, D., Schragl, K., Weil, M., Gaertner, P., & Enev, V. S. (2022). Efforts toward the Total Synthesis of Elisabethin A. Journal of Organic Chemistry, 87(22), 15333–15349. https://doi.org/10.1021/acs.joc.2c01914
We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an "underdeveloped" Claisen rearrangement of an aryl dienyl ether.
