Short-step and scalable synthesis of (+/-)-cytoxazone.
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.
Asano
Masayoshi
M
Department of Chemistry, Keio University, Yokohama, Japan.
Nagasawa
Chiaki
C
Suzuki
Masumi
M
Nishiyama
Shigeru
S
Sugai
Takeshi
T
D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010080:Oxazoles; C117832:cytoxazone