Short-step and scalable synthesis of (±)-cytoxazone

Masayoshi Asano, Chiaki Nagasawa, Masumi Suzuki, Shigeru Nishiyama, Takeshi Sugai

Research output: Contribution to journalArticle

11 Citations (Scopus)

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-H 2O2-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.

Original languageEnglish
Pages (from-to)145-148
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume69
Issue number1
DOIs
Publication statusPublished - 2005 Jan

Fingerprint

olefin
azides
Sodium Azide
Epoxidation
Azides
Epoxy Compounds
Alkenes
epoxides
Modulators
Olefins
Alcohols
cytokines
alcohols
Ions
ions
Cytokines
synthesis
cytoxazone

Keywords

  • Azidohydroxylation
  • Cytoxazone
  • Deaminocyclization
  • Nitrosation
  • Oxazolidinone

ASJC Scopus subject areas

  • Bioengineering
  • Biotechnology
  • Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology
  • Food Science

Cite this

Short-step and scalable synthesis of (±)-cytoxazone. / Asano, Masayoshi; Nagasawa, Chiaki; Suzuki, Masumi; Nishiyama, Shigeru; Sugai, Takeshi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 69, No. 1, 01.2005, p. 145-148.

Research output: Contribution to journalArticle

Asano, Masayoshi ; Nagasawa, Chiaki ; Suzuki, Masumi ; Nishiyama, Shigeru ; Sugai, Takeshi. / Short-step and scalable synthesis of (±)-cytoxazone. In: Bioscience, Biotechnology and Biochemistry. 2005 ; Vol. 69, No. 1. pp. 145-148.
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