title: An enantiospecific route towards taiwaniaquinoids. First synthesis of (-)-taiwaniaquinone H and (-)-dichroanone.
abstract: A new methodology for the enantiospecific synthesis of taiwaniaquinoids, based on a thermal 6pi electrocyclization, is reported. Under this procedure, 4a-methylhexahydrofluorene terpenoids bearing an A/B trans-configuration has been prepared for the first time. This methodology also makes it feasible to synthesize taiwaniaquinoids with an A/B cis-configuration and 4a-methyltetrahydrofluorene terpenoids. Accordingly, the first synthesis of (-)-taiwaniaquinone G, (-)-taiwaniaquinone H and (-)-dichroanone has been achieved.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain. eamr@ugr.es
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
authors.forename: Eduardo
authors.initials: E
authors.lastname: Cabrera
authors.forename: Esteban
authors.initials: E
authors.lastname: Alvarez
authors.forename: Ali
authors.initials: A
authors.lastname: Haidour
authors.forename: Jose Miguel
authors.initials: JM
authors.lastname: Ramos
authors.forename: Ramón
authors.initials: R
authors.lastname: Alvarez-Manzaneda
authors.forename: Yahia
authors.initials: Y
authors.lastname: Charrah
authors.forename: Hakima
authors.initials: H
authors.lastname: Es-Samti
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D008722:Methods; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis
chemical_list: D004224:Diterpenes; D013729:Terpenes; C516091:dichroanone; C516088:taiwaniaquinone H