title: Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis.
abstract: The first synthesis of a labdane-type diterpenoid isolated from Isodon yuennanensis was achieved in fourteen steps from commercially available starting material, (+)-sclareolide. The synthesis features the Barton nitrite ester reaction to introduce an oxime at the angular methyl group and the Jones oxidation to construct the lactone segment. By comparison of the optical rotation of our synthetic sample and the natural sample, the absolute stereochemistry of the natural diterpenoid has been determined.
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China. chembliu@scu.edu.cn.
authors.forename: Heping
authors.initials: H
authors.lastname: Deng
authors.forename: Wei
authors.initials: W
authors.lastname: Cao
authors.forename: Zhijiang
authors.initials: Z
authors.lastname: Zhang
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D008689:Methacrylates / Q000737:chemistry*; D008968:Molecular Conformation; D009566:Nitrates / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry*; D012969:Sodium Fluoride / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C473099:Isodan; D008689:Methacrylates; D009566:Nitrates; C433017:labdane; D012969:Sodium Fluoride