Enantio- and diastereocontrolled synthesis of an angular triquinane sesquiterpene (+)-arnicenone.
[figure: see text] (+)-Arnicenone, a sesquiterpene of an angular triquinane isolated from Arnica plants, has been synthesized for the first time in an enantiocontrolled manner from a synthetic equivalent of chiral 2-hydroxymethylcyclopentadienone to determine the absolute configuration of the natural product as 1R,3aR,5aS,8aR.
Iura
Y
Y
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Sugahara
T
T
Ogasawara
K
K
D018650:Arnica / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D010946:Plants, Medicinal; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C432005:arnicenone