An enantiospecific route towards taiwaniaquinoids. First synthesis of (-)-taiwaniaquinone H and (-)-dichroanone.
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.
Alvarez-Manzaneda
Enrique
E
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain. eamr@ugr.es
Chahboun
Rachid
R
Cabrera
Eduardo
E
Alvarez
Esteban
E
Haidour
Ali
A
Ramos
Jose Miguel
JM
Alvarez-Manzaneda
Ramón
R
Charrah
Yahia
Y
Es-Samti
Hakima
H
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D008722:Methods; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis
D004224:Diterpenes; D013729:Terpenes; C516091:dichroanone; C516088:taiwaniaquinone H