title: Divergent total synthesis of triptolide, triptonide, tripdiolide, 16-hydroxytriptolide, and their analogues.
abstract: A divergent route was developed for the formal total synthesis of triptolide, triptonide, and tripdiolide, as well as a total synthesis of 16-hydroxytriptolide and their analogues in an enantioselective form. Common advanced intermediate 5 was concisely assembled by employing an indium(III)-catalyzed cationic polycyclization reaction and a palladium-catalyzed carbonylation-lactone formation reaction as key steps. This advanced intermediate was readily converted to the above natural products by using palladium-catalyzed cross-coupling or the Claisen rearrangement reaction as key steps. Additionally, preliminary structure-cytotoxic activity relationship studies of C13 suggested that it might be a new modification site that could still retain the cytotoxicity.
authors.affiliation: Department of Medical Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Zhangjiang Hi-Tech Park, Shanghai 201203, P.R. China.
authors.forename: Hongtao
authors.initials: H
authors.lastname: Xu
authors.forename: Huanyu
authors.initials: H
authors.lastname: Tang
authors.forename: Huijin
authors.initials: H
authors.lastname: Feng
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007204:Indium / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004224:Diterpenes; D004852:Epoxy Compounds; D007783:Lactones; D010616:Phenanthrenes; D014315:Triterpenes; D007204:Indium; C076300:16-hydroxytriptolide; C001899:triptolide; C084079:triptonide; D010165:Palladium; C001898:tripdiolide