Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Takahisa Ogamino; Rika Obata; Shigeru Nishiyama

doi:10.1016/j.tetlet.2005.11.097

Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Takahisa Ogamino, Rika Obata, Shigeru Nishiyama

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

43 Citations (Scopus)

Abstract

Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives.

Original language	English
Pages (from-to)	727-731
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2005.11.097
Publication status	Published - 2006 Jan 30
Externally published	Yes

Keywords

Aerothionin
Bromotyrosine
Diastereomeric separation
Spiroisoxazoline

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.2005.11.097

Cite this

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title = "Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative",

abstract = "Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives.",

keywords = "Aerothionin, Bromotyrosine, Diastereomeric separation, Spiroisoxazoline",

author = "Takahisa Ogamino and Rika Obata and Shigeru Nishiyama",

note = "Funding Information: This work was supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}Keio Life Conjugate Chemistry,{\textquoteright} as well as Scientific Research C from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. The authors are grateful to the COE program and JSPS Research Fellowships for Young Scientists for financial support to T.O.",

year = "2006",

month = jan,

day = "30",

doi = "10.1016/j.tetlet.2005.11.097",

language = "English",

volume = "47",

pages = "727--731",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "5",

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TY - JOUR

T1 - Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

AU - Ogamino, Takahisa

AU - Obata, Rika

AU - Nishiyama, Shigeru

N1 - Funding Information: This work was supported by Grant-in-Aid for the 21st Century COE program ‘Keio Life Conjugate Chemistry,’ as well as Scientific Research C from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. The authors are grateful to the COE program and JSPS Research Fellowships for Young Scientists for financial support to T.O.

PY - 2006/1/30

Y1 - 2006/1/30

N2 - Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives.

AB - Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives.

KW - Aerothionin

KW - Bromotyrosine

KW - Diastereomeric separation

KW - Spiroisoxazoline

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DO - 10.1016/j.tetlet.2005.11.097

M3 - Article

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SN - 0040-4039

VL - 47

SP - 727

EP - 731

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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