Synthesis of aurachins B and H

Kazuki Takahashi; Shigefumi Kuwahara; Masaru Enomoto

doi:10.1080/09168451.2017.1325711

Synthesis of aurachins B and H

Kazuki Takahashi, Shigefumi Kuwahara, Masaru Enomoto

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

1 Citation (Scopus)

Abstract

The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitro-toluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide.

Original language	English
Pages (from-to)	1466-1469
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	81
Issue number	8
DOIs	https://doi.org/10.1080/09168451.2017.1325711
Publication status	Published - 2017

Keywords

Aurachin B
Aurachin H
Quinoline N-oxide
Quinoline antibiotics
Reductive cyclization

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1080/09168451.2017.1325711

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title = "Synthesis of aurachins B and H",

abstract = "The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitro-toluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide.",

keywords = "Aurachin B, Aurachin H, Quinoline N-oxide, Quinoline antibiotics, Reductive cyclization",

author = "Kazuki Takahashi and Shigefumi Kuwahara and Masaru Enomoto",

note = "Funding Information: We thank Prof Yamashita, Dr Cho and Ms Taguchi (Tohoku University) for their help in measuring NMR and MS spectra. After our manuscript was sent to the journal, a synthesis of aurachins A and B was published (See, Ref 19). This work was financially supported by JSPS KAKENHI [grant number 16K07708]. Publisher Copyright: {\textcopyright} 2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2017",

doi = "10.1080/09168451.2017.1325711",

language = "English",

volume = "81",

pages = "1466--1469",

journal = "Bioscience, Biotechnology and Biochemistry",

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number = "8",

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T1 - Synthesis of aurachins B and H

AU - Takahashi, Kazuki

AU - Kuwahara, Shigefumi

AU - Enomoto, Masaru

N1 - Funding Information: We thank Prof Yamashita, Dr Cho and Ms Taguchi (Tohoku University) for their help in measuring NMR and MS spectra. After our manuscript was sent to the journal, a synthesis of aurachins A and B was published (See, Ref 19). This work was financially supported by JSPS KAKENHI [grant number 16K07708]. Publisher Copyright: © 2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017

Y1 - 2017

N2 - The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitro-toluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide.

AB - The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitro-toluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide.

KW - Aurachin B

KW - Aurachin H

KW - Quinoline N-oxide

KW - Quinoline antibiotics

KW - Reductive cyclization

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JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 8

ER -

Synthesis of aurachins B and H

Abstract

Keywords

ASJC Scopus subject areas

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