Thanks to phytotherapy, it has been found that many natural products can help the treatment of different diseases. In particular, (-)-parthenolide, a sesquiterpene lactone from the germacranolide class coming from feverfew, is a promising antagonist of endometriosis, an highly diffuse feminine disease which causes chronic symptoms that are often incapacitating both physically and psychologically. Therefore, due to its highly interesting pharmacological activity and its shortage in the plant’s extracts, the first total synthesis of (-)-parthenolide, under stereochemical control, has been took on through a highly selective synthetic pathway that aims to the least number of synthetic steps as compared to the few already existent semisynthesis. Control over stereochemistry will be possible through using 4 key reactions and, eventually, thanks to an early-stage divergence point, the synthetic strategy will reconverge again giving a “circular synthesis” aimed to reducing resources waste and minimizing reactants usage for a greener perspective.
Total synthesis of (-)-parthenolide through stereochemical control / Celio, Lorenzo; Marchetto, Martina; Rendeli, Dario; Vetica, Fabrizio; Maria Migneco, Luisa; Leonelli, Francesca. - (2022). (Intervento presentato al convegno XL Convegno Nazionale della Divisione di Chimica Organica, CDCO Palermo 2022 tenutosi a Palermo, Italy).
Total synthesis of (-)-parthenolide through stereochemical control
Lorenzo Celio
Primo
;Martina Marchetto;Fabrizio Vetica;Francesca Leonelli
Supervision
2022
Abstract
Thanks to phytotherapy, it has been found that many natural products can help the treatment of different diseases. In particular, (-)-parthenolide, a sesquiterpene lactone from the germacranolide class coming from feverfew, is a promising antagonist of endometriosis, an highly diffuse feminine disease which causes chronic symptoms that are often incapacitating both physically and psychologically. Therefore, due to its highly interesting pharmacological activity and its shortage in the plant’s extracts, the first total synthesis of (-)-parthenolide, under stereochemical control, has been took on through a highly selective synthetic pathway that aims to the least number of synthetic steps as compared to the few already existent semisynthesis. Control over stereochemistry will be possible through using 4 key reactions and, eventually, thanks to an early-stage divergence point, the synthetic strategy will reconverge again giving a “circular synthesis” aimed to reducing resources waste and minimizing reactants usage for a greener perspective.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.