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

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

doi:10.1271/bbb.69.145

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

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	145-148
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	69
Issue number	1
DOIs	https://doi.org/10.1271/bbb.69.145
Publication status	Published - 2005 Jan

Keywords

Azidohydroxylation
Cytoxazone
Deaminocyclization
Nitrosation
Oxazolidinone

ASJC Scopus subject areas

General Medicine

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10.1271/bbb.69.145

Cite this

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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-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.",

keywords = "Azidohydroxylation, Cytoxazone, Deaminocyclization, Nitrosation, Oxazolidinone",

author = "Masayoshi Asano and Chiaki Nagasawa and Masumi Suzuki and Shigeru Nishiyama and Takeshi Sugai",

note = "Funding Information: This work formed part of the 21st century COE program (Keio LCC) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. Keio Gijuku Funding for the advancement of education and research is also acknowledged with thanks.",

year = "2005",

month = jan,

doi = "10.1271/bbb.69.145",

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pages = "145--148",

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AU - Asano, Masayoshi

AU - Nagasawa, Chiaki

AU - Suzuki, Masumi

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

N1 - Funding Information: This work formed part of the 21st century COE program (Keio LCC) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. Keio Gijuku Funding for the advancement of education and research is also acknowledged with thanks.

PY - 2005/1

Y1 - 2005/1

N2 - 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.

AB - 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.

KW - Azidohydroxylation

KW - Cytoxazone

KW - Deaminocyclization

KW - Nitrosation

KW - Oxazolidinone

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UR - https://www.scopus.com/pages/publications/15244354409#tab=citedBy

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AN - SCOPUS:15244354409

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VL - 69

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JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 1

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

Abstract

Keywords

ASJC Scopus subject areas

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