Diastereoselective formal total synthesis of (+/-)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane.
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.
Goncalves
Sylvie
S
University of Strasbourg, Faculty of Pharmacy, Laboratory of Functional ChemoSystems CNRS/UMR 7199, 74 route du Rhin BP60024, 67400 Illkirch, France.
Hellier
Paul
P
Nicolas
Marc
M
Wagner
Alain
A
Baati
Rachid
R
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
D002412:Cations; D004224:Diterpenes; D004852:Epoxy Compounds; D006571:Heterocyclic Compounds; D010616:Phenanthrenes; C001899:triptolide; C012948:1,3-dithiolane