Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement

Masahiro Masuda; Natsuki Sakurai; Yusuke Ogura; Tetsuji Murase; Tsuneomi Kawasaki; Shohei Aiba; Naoki Mori; Hidenori Watanabe; Hirosato Takikawa

doi:10.1016/j.tetlet.2020.151825

Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement

Masahiro Masuda, Natsuki Sakurai, Yusuke Ogura, Tetsuji Murase, Tsuneomi Kawasaki, Shohei Aiba, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

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

Abstract

Neurymenolides, α-pyrone macrolides isolated from the Fijian red alga Neurymenia fraxinifolia, are anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium compounds. In this study, the macrocyclic core of neurymenolide A was constructed in an enantioselective manner by employing Claisen rearrangement as the key step.

Original language	English
Article number	151825
Journal	Tetrahedron Letters
Volume	61
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2020.151825
Publication status	Published - 2020 Apr 30
Externally published	Yes

Keywords

Claisen rearrangement
Macrolides
Neurymenolides
α-Pyrone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.151825

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title = "Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement",

abstract = "Neurymenolides, α-pyrone macrolides isolated from the Fijian red alga Neurymenia fraxinifolia, are anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium compounds. In this study, the macrocyclic core of neurymenolide A was constructed in an enantioselective manner by employing Claisen rearrangement as the key step.",

keywords = "Claisen rearrangement, Macrolides, Neurymenolides, α-Pyrone",

author = "Masahiro Masuda and Natsuki Sakurai and Yusuke Ogura and Tetsuji Murase and Tsuneomi Kawasaki and Shohei Aiba and Naoki Mori and Hidenori Watanabe and Hirosato Takikawa",

note = "Funding Information: We thank Prof. Ken Ishigami (Tokyo University of Agriculture) for his helpful discussions. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = apr,

day = "30",

doi = "10.1016/j.tetlet.2020.151825",

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

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T1 - Studies toward the enantioselective synthesis of neurymenolide A

T2 - Construction of the macrocyclic core via Claisen rearrangement

AU - Masuda, Masahiro

AU - Sakurai, Natsuki

AU - Ogura, Yusuke

AU - Murase, Tetsuji

AU - Kawasaki, Tsuneomi

AU - Aiba, Shohei

AU - Mori, Naoki

AU - Watanabe, Hidenori

AU - Takikawa, Hirosato

PY - 2020/4/30

Y1 - 2020/4/30

N2 - Neurymenolides, α-pyrone macrolides isolated from the Fijian red alga Neurymenia fraxinifolia, are anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium compounds. In this study, the macrocyclic core of neurymenolide A was constructed in an enantioselective manner by employing Claisen rearrangement as the key step.

AB - Neurymenolides, α-pyrone macrolides isolated from the Fijian red alga Neurymenia fraxinifolia, are anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium compounds. In this study, the macrocyclic core of neurymenolide A was constructed in an enantioselective manner by employing Claisen rearrangement as the key step.

KW - Claisen rearrangement

KW - Macrolides

KW - Neurymenolides

KW - α-Pyrone

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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