title: Stereoselective syntheses of four diastereomers of 3,9,12-trihydroxycalamenene via a benzobicyclo[3.3.1] intermediate.
abstract: The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel-Crafts-type Michael addition of alpha,beta-unsaturated lactones.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, 730000, People's Republic of China.
authors.forename: Yongquan
authors.initials: Y
authors.lastname: Sun
authors.forename: Binxun
authors.initials: B
authors.lastname: Yu
authors.forename: Xiaolei
authors.initials: X
authors.lastname: Wang
authors.forename: Shibing
authors.initials: S
authors.lastname: Tang
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
authors.forename: Xinfu
authors.initials: X
authors.lastname: Pan
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D007783:Lactones; D000081223:Polycyclic Sesquiterpenes; D013729:Terpenes; C502644:calamenene