title: Full stereochemical assignment and synthesis of the potent anthelmintic pyrrolobenzoxazine natural product CJ-12662.
abstract: The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
authors.forename: Charles
authors.initials: C
authors.lastname: Didier
authors.forename: Douglas J
authors.initials: DJ
authors.lastname: Critcher
authors.forename: Nigel D
authors.initials: ND
authors.lastname: Walshe
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kojima
authors.forename: Yuji
authors.initials: Y
authors.lastname: Yamauchi
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
mesh_terms: D000871:Anthelmintics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000871:Anthelmintics; D048588:Benzoxazines; C494002:CJ 12662; D011758:Pyrroles; D013729:Terpenes