title: Short-step and scalable synthesis of (+/-)-cytoxazone.
abstract: A five-step and scalable synthesis of racemic cytoxazone, a novel cytokine modulator, was accomplished in a total yield of 51% from p-methoxycinnamyl alcohol without any protective groups. The keystep was the new one-pot azidohydroxylation procedure by the combined use of NaN3-H2O2-CH3CN. The epoxidation of an olefin by means of an in situ-formed iminohydroperoxide worked well, accompanied by the concomitant regioselective ring opening reaction of the resulting highly reactive epoxide with an azide ion.
authors.affiliation: Department of Chemistry, Keio University, Yokohama, Japan.
authors.forename: Masayoshi
authors.initials: M
authors.lastname: Asano
authors.forename: Chiaki
authors.initials: C
authors.lastname: Nagasawa
authors.forename: Masumi
authors.initials: M
authors.lastname: Suzuki
authors.forename: Shigeru
authors.initials: S
authors.lastname: Nishiyama
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sugai
mesh_terms: D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D010080:Oxazoles; C117832:cytoxazone