title: Synthesis and structural revision of a brominated sesquiterpenoid, aldingenin C.
abstract: This paper describes a short step synthesis of the proposed structure for aldingenin C from trans-limonene oxide. The tetrahydropyran-fused 2-oxabicyclo[3.2.2]nonane skeleton as the structural feature was constructed by an intramolecular epoxide-opening reaction and a brominative cyclization. The spectral data of the synthetic compound did not match those of the natural product reported. Re-examination of the reported NMR data using new CAST/CNMR Structure Elucidator suggests that the structure of aldingenin C should be revised to that of known caespitol.
authors.affiliation: RIKEN , Wako, Saitama 351-0198, Japan.
authors.forename: Shunya
authors.initials: S
authors.lastname: Takahashi
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yasuda
authors.forename: Takemichi
authors.initials: T
authors.lastname: Nakamura
authors.forename: Ken
authors.initials: K
authors.lastname: Hatano
authors.forename: Koji
authors.initials: K
authors.lastname: Matsuoka
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
mesh_terms: D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D054879:Halogenation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D012717:Sesquiterpenes; C514267:aldingenin C; C028940:limonene-1,2-epoxide