Schachamayr, D. (2024). Towards the total synthesis of euphosalicin [Dissertation, Technische Universität Wien]. reposiTUm. https://doi.org/10.34726/hss.2024.20597
total synthesis; asymmetric synthesis; biomimetic synthesis
de
total synthesis; asymmetric synthesis; biomimetic synthesis
en
Abstract:
Euphosalicin is a natural product that was extracted from the plant Euphorbia salicifolia in 2001 and is a member of the Jatrophane class. Jatrophanes are known for their potent biological activities, particularly in the reversal of multidrug resistance (MDR). Initial tests have demonstrated that Euphosalicin exhibits significant potential in this regard, hinting at its possible utility in various cancer treatments. However, from several kilograms of plant material only a few milligrams of the compound can be isolated, which shows the need for a synthetic approach to facilitate further biological investigations. The primary objective of this dissertation project is to achieve the total synthesis of Euphosalicin. Success in this endeavor would not only enable additional biological experiments but also pave the way for the synthesis of derivatives of the mentioned compound. These derivatives could prove vital in identifying the specific structural elements responsible for the compound's biological activity, thereby aiding in the development of novel drugs. The retrosynthetic plan involves transformations such as asymmetric dihydroxylations, an enyne metathesis, and a ring-closing metathesis as the key steps. This dissertation focuses on exploring and optimizing these transformations to accomplish the total synthesis of Euphosalicin and to gain insights for the potential synthesis of other jatrophanes as well.
