title: Diastereoselective formal total synthesis of (+/-)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane.
abstract: A concise and diastereoselective formal total synthesis of triptolide, a natural product with a wide range of biological properties, is described. The key reaction is an unprecedented 6-endo-Trig cationic cyclization of a 2-alkenyl-1,3-dithiolane precursor induced by TMSOTf as Lewis acid.
authors.affiliation: University of Strasbourg, Faculty of Pharmacy, Laboratory of Functional ChemoSystems CNRS/UMR 7199, 74 route du Rhin BP60024, 67400 Illkirch, France.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Goncalves
authors.forename: Paul
authors.initials: P
authors.lastname: Hellier
authors.forename: Marc
authors.initials: M
authors.lastname: Nicolas
authors.forename: Alain
authors.initials: A
authors.lastname: Wagner
authors.forename: Rachid
authors.initials: R
authors.lastname: Baati
mesh_terms: D002412:Cations / Q000737:chemistry; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002412:Cations; D004224:Diterpenes; D004852:Epoxy Compounds; D006571:Heterocyclic Compounds; D010616:Phenanthrenes; C001899:triptolide; C012948:1,3-dithiolane