472-37-7Relevant academic research and scientific papers
TERPENOIDS FROM LEAVES OF JUNIPERUS THURIFERA
San Feliciano, A.,Medarde, M.,Lopez, J. L.,Corral, J. M. Miguel Del,Puebla, P.,Barrero, A. F.
, p. 2241 - 2248 (1988)
Juniperus thurifera; Cupressaceae; diterpenoids; labdanes; pimaranes; abietanes; chemotaxonomy.Nineteen diterpenoids of the labdane, pimarane and abietane skeletons and four known sesqiterpenoids were isolated from Juniperus thurifera leaves.Thirteen of these diterpenoids are described for the first time as natural products.Their structures were elucidated principally by NMR techniques and chemical transformations.
Synthesis of (+)-Hinokiol, (+)-Hinokione, (+)-Salviol, and (+)-2-Oxoferruginol
Matsumoto, Takashi,Usui, Shuji,Kawashima, Hiroyuki,Mitsuki, Masanori
, p. 581 - 584 (2007/10/02)
Reduction of abieta-5,8,11,13-tetraen-3-one with lithium aluminium hydride afforded the corresponding alcohol, which was submitted to catalytic hydrogenation to yield abieta-8,11,13-trien-3β-ol (7) together with its 5βH-isomer.Acetylation of 7, followed by the Friedel-Crafts acylation, afforded 3β-acetoxy-12-acetylabieta-8,11,13-triene.This compound was converted into 3β,12-diacetoxyabieta-8,11,13-triene (11) by the Baeyer-Villiger oxidation.Treatment of 11 with lithium aluminium hydride yielded hinokiol, which was oxidized to hinokione.Subsequently, hinokiol was methylated and the resulting 12-methyl ether was dehydrated to afford 12-methoxyabieta-2,8,11,13-tetraene.The tetraene was then submitted to hydroboration-oxidation to give 12-methoxyabieta-8,11,13-trien-2α-ol (15) which, on demethylation with ethanethiol and anhydrous aluminium chloride, afforded salviol.Oxidation of 15 with pyridinium chlorochromate, followed by demethylation, gave 2-oxoferruginol.
