title: Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon.
abstract: The synthesis of a novel hydrocarbon, dibarrelane, has been accomplished in 11 steps via an intramolecular REDDA reaction of a masked o-benzoquinone, followed by Clemmensen reduction and Barton decarboxylation. The twisted structure of the tetracyclic dibarrelane skeleton was also clarified via X-ray crystallography. Finally, it was proposed that dibarrelane has C2 symmetry rather than C(2v) symmetry.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science , 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Suzuki
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Okuyama
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Takano
authors.forename: Shinya
authors.initials: S
authors.lastname: Suzuki
authors.forename: Isao
authors.initials: I
authors.lastname: Shimizu
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D006838:Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D016227:Benzoquinones; D034242:Cyclooctanes; D006838:Hydrocarbons; D011084:Polycyclic Aromatic Hydrocarbons; D011083:Polycyclic Compounds; C000592422:dibarrelane; C004532:quinone