Synthesis of bacilosarcins B and C

Kazuki Kurasawa; Shigefumi Kuwahara; Masaru Enomoto

doi:10.1016/j.tetlet.2016.09.090

Synthesis of bacilosarcins B and C

Kazuki Kurasawa, Shigefumi Kuwahara, Masaru Enomoto

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

10 Citations (Scopus)

Abstract

The first synthesis of bacilosarcin C, a member of amicoumacin family of natural product isolated from the culture broth of a marine bacterium, has been achieved in 2 steps by diastereoselective reductive amination of amicoumacin C with 2,3-butanedione followed by hydrolysis of the resulting N-alkylated lactone intermediate. Ammonolysis of the intermediate, on the other hand, led to an improved synthesis of bacilosarcin B, an amide congener of bacilosarcin C.

Original language	English
Pages (from-to)	4997-4999
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2016.09.090
Publication status	Published - 2016

Keywords

Amicoumacin
Bacilosarcin
Isocoumarin
Reductive amination
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2016.09.090

Cite this

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title = "Synthesis of bacilosarcins B and C",

abstract = "The first synthesis of bacilosarcin C, a member of amicoumacin family of natural product isolated from the culture broth of a marine bacterium, has been achieved in 2 steps by diastereoselective reductive amination of amicoumacin C with 2,3-butanedione followed by hydrolysis of the resulting N-alkylated lactone intermediate. Ammonolysis of the intermediate, on the other hand, led to an improved synthesis of bacilosarcin B, an amide congener of bacilosarcin C.",

keywords = "Amicoumacin, Bacilosarcin, Isocoumarin, Reductive amination, Total synthesis",

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

note = "Funding Information: We are grateful to professor P.-Y. Qian (Hong Kong University of Science and Technology) for providing valuable information about the spectral data of natural bacilosarcin C. We also thank Ms. Yuka Taguchi (Tohoku University) for her help in measuring NMR and MS spectra. This work was financially supported by JSPS KAKENHI (Grant Number 16K07708 ). Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.09.090",

language = "English",

volume = "57",

pages = "4997--4999",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "45",

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TY - JOUR

T1 - Synthesis of bacilosarcins B and C

AU - Kurasawa, Kazuki

AU - Kuwahara, Shigefumi

AU - Enomoto, Masaru

N1 - Funding Information: We are grateful to professor P.-Y. Qian (Hong Kong University of Science and Technology) for providing valuable information about the spectral data of natural bacilosarcin C. We also thank Ms. Yuka Taguchi (Tohoku University) for her help in measuring NMR and MS spectra. This work was financially supported by JSPS KAKENHI (Grant Number 16K07708 ). Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - The first synthesis of bacilosarcin C, a member of amicoumacin family of natural product isolated from the culture broth of a marine bacterium, has been achieved in 2 steps by diastereoselective reductive amination of amicoumacin C with 2,3-butanedione followed by hydrolysis of the resulting N-alkylated lactone intermediate. Ammonolysis of the intermediate, on the other hand, led to an improved synthesis of bacilosarcin B, an amide congener of bacilosarcin C.

AB - The first synthesis of bacilosarcin C, a member of amicoumacin family of natural product isolated from the culture broth of a marine bacterium, has been achieved in 2 steps by diastereoselective reductive amination of amicoumacin C with 2,3-butanedione followed by hydrolysis of the resulting N-alkylated lactone intermediate. Ammonolysis of the intermediate, on the other hand, led to an improved synthesis of bacilosarcin B, an amide congener of bacilosarcin C.

KW - Amicoumacin

KW - Bacilosarcin

KW - Isocoumarin

KW - Reductive amination

KW - Total synthesis

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DO - 10.1016/j.tetlet.2016.09.090

M3 - Article

AN - SCOPUS:84991372820

SN - 0040-4039

VL - 57

SP - 4997

EP - 4999

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Synthesis of bacilosarcins B and C

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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