(-)-parthenolide, a sesquiterpene lactone from the germacranolide class that comes from the plant feverfew (Tanacetum parthenium), is a promising antagonist of endometriosis, an highly diffuse feminine disease in which endometrium’s cells grow outside of the uterus, causing chronic symptoms that are often incapacitating both physically and psychologically. Therefore, due to its pharmacological activity and its shortage in the plant’s extracts, the first enantio and diastereoselective total synthesis of (-)-parthenolide has been approached through a highly selective synthetic strategy. This involves the application of “classical” organic chemistry reactions and the least number of synthetic steps as compared to the few already existent semisynthesis. Stereochemical control is made possible through 4 key steps and, moreover, after an early-stage divergence point the two synthetic paths will reconnect together in a juncture to obtain a “circular synthesis”, reducing resources waste and minimizing reactants for a greener perspective

Enantio and diastereoselective total synthesis of (-)-parthenolide / Celio, Lorenzo; Leonelli, Francesca; Marchetto, Martina; Rendeli, Dario; Vetica, Fabrizio; Maria Migneco, Luisa. - (2022). (Intervento presentato al convegno The First Symposium for YouNg Chemists: Innovation and Sustainability (SYNC2022) tenutosi a Rome, Italy).

Enantio and diastereoselective total synthesis of (-)-parthenolide

Lorenzo Celio
Primo
;
Francesca Leonelli
Supervision
;
Martina Marchetto;Fabrizio Vetica;
2022

Abstract

(-)-parthenolide, a sesquiterpene lactone from the germacranolide class that comes from the plant feverfew (Tanacetum parthenium), is a promising antagonist of endometriosis, an highly diffuse feminine disease in which endometrium’s cells grow outside of the uterus, causing chronic symptoms that are often incapacitating both physically and psychologically. Therefore, due to its pharmacological activity and its shortage in the plant’s extracts, the first enantio and diastereoselective total synthesis of (-)-parthenolide has been approached through a highly selective synthetic strategy. This involves the application of “classical” organic chemistry reactions and the least number of synthetic steps as compared to the few already existent semisynthesis. Stereochemical control is made possible through 4 key steps and, moreover, after an early-stage divergence point the two synthetic paths will reconnect together in a juncture to obtain a “circular synthesis”, reducing resources waste and minimizing reactants for a greener perspective
2022
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1668628
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact