title: General access to taiwaniaquinoids based on a hypothetical abietane C7-C8 cleavage biogenetic pathway.
abstract: A new strategy for synthesizing taiwaniaquinoids, a group of terpenoids with an unusual rearranged 5(6→7) or 6-nor-5(6→7)abeo-abietane skeleton, which exhibit promising biological activities, is reported. The procedure, based on the cleavage of the C7-C8 double bond of abietane diterpenes, is the only one yet reported for synthesizing C(20) taiwaniaquinoids bearing a carbon function on the cyclopentane B ring; it is also applicable to the synthesis of the wide variety of existing taiwaniaquinoids. Utilizing this, (-)-taiwaniaquinone A, F, G, and H, (-)-taiwaniaquinol B, and (-)-dichroanone have been synthesized from (+)-abietic acid. The versatility of this strategy allows us to propose the abietane C7-C8 cleavage as a possible biosynthetic pathway to this type of rearranged diterpenes; this proposal seems to be supported by phytochemical evidence.
authors: Departamento de Quimica Orgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain.
authors: Rubén
authors: R
authors: Tapia
authors: Juan J
authors: JJ
authors: Guardia
authors: Esteban
authors: E
authors: Alvarez
authors: Ali
authors: A
authors: Haidöur
authors: Jose M
authors: JM
authors: Ramos
authors: Ramón
authors: R
authors: Alvarez-Manzaneda
authors: Rachid
authors: R
authors: Chahboun
authors: Enrique
authors: E
authors: Alvarez-Manzaneda
mesh_terms: D045784:Abietanes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D045784:Abietanes; D004224:Diterpenes; D013729:Terpenes; C505702:taiwaniaquinol B