15404-32-7Relevant academic research and scientific papers
CONFIGURATION OF NATURAL 9-HYDROXYFUROEREMOPHILANE, ITS 9-HYDROXY EPIMER AND FURANOPETASIN: NMR AND CD STUDIES
Novotny, Ladislav,Budesinsky, Milos,Jizba, Josef,Harmatha, Juraj,Lukes, Vit,et al.
, p. 1786 - 1802 (2007/10/02)
The conformation and configuration analysis of cis- and trans-furoeremophilanes with hydroxy group in position 9, using 1H NMR and CD spectra, is discussed.Some steroid derivatives were used as model for CD study.A combination of both spectral methods gives complementary results.For natural 9-hydroxyfuroeremophilane the configuration 9β-OH was unequivocally proved and the originally proposed structure of furanopetasin corrected to VII.
Synthetic Study on Several Eremophilane Sesquiterpenes using a Common Intermediate
Hagiwara, Hisahiro,Uda, Hisashi,Kodama, Tsutomu
, p. 963 - 977 (2007/10/02)
The syntheses of racemic ishwarane (6), dehydrofukinone (7), hydroxyeremophilone (8), 9,10-dehydrofuranoeremophilane (9), 10α-furanoeremophilone (10), and 9,10-dehydrofuranoeremophil-1-one (11) from a common intermediate, cis-4,4a,5,6,7,8-hexahydro-4a,5-dimethylnaphthalen-2(3H)-one (5), are described.For the synthesis of ishwarane (6) the key step is sequential Michael addition and displacement of the enolate of the isomeric octalone, cis-4a,5,6,7,8a-hexahydro-4a,5-dimethylnaphthalen-1(4H)-one (4), prepared from the octalone (5), with methyl α-bromoacrylate; for the syntheses of the other terpenes (7)-(11) the key step is the zinc chloride-assisted aldol condensation of the enolates of the octalone (5) and the suitably functionalised derivatives with acetone or acetonyl tetrahydropyranyl ether.
