Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide

Hiroyoshi Takamura; Yuichiro Kadonaga; Isao Kadota; Daisuke Uemura

doi:10.1016/j.tetlet.2010.03.014

Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide

Hiroyoshi Takamura, Yuichiro Kadonaga, Isao Kadota, Daisuke Uemura

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

9 Citations (Scopus)

Abstract

Symbiodinolide is a polyol macrolide isolated from the marine dinoflagellate Symbiodinium sp. in 2007. The C14-C24 fragment of symbiodinolide possessing the 17R/18R/21R absolute configuration, which was obtained as one of the degraded products of symbiodinolide, was synthesized stereoselectively from cis-2-butene-1,4-diol. The detailed comparison of the synthetic product with the degraded product in the spectroscopic data confirmed that the stereostructure of the C14-C24 fragment was 17R, 18R, and 21R.

Original language	English
Pages (from-to)	2603-2605
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2010.03.014
Publication status	Published - May 12 2010

Keywords

Polyol macrolide
Stereoselective synthesis
Structural confirmation
Symbiodinolide

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.2010.03.014

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title = "Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide",

abstract = "Symbiodinolide is a polyol macrolide isolated from the marine dinoflagellate Symbiodinium sp. in 2007. The C14-C24 fragment of symbiodinolide possessing the 17R/18R/21R absolute configuration, which was obtained as one of the degraded products of symbiodinolide, was synthesized stereoselectively from cis-2-butene-1,4-diol. The detailed comparison of the synthetic product with the degraded product in the spectroscopic data confirmed that the stereostructure of the C14-C24 fragment was 17R, 18R, and 21R.",

keywords = "Polyol macrolide, Stereoselective synthesis, Structural confirmation, Symbiodinolide",

author = "Hiroyoshi Takamura and Yuichiro Kadonaga and Isao Kadota and Daisuke Uemura",

note = "Funding Information: We are grateful to Dr. C. Han and Mr. Y. Yamano (Nagoya University) for the valuable discussions. We appreciate Okayama Foundation for Science and Technology, NOVARTIS Foundation (Japan) for the Promotion of Science, and WESCO Scientific Promotion Foundation for their financial supports. This research was supported by Grant-in-Aid for Young Scientists (B) ( 19710184 and 21710231 ) from Japan Society for the Promotion of Science (JSPS) and The Ministry of Education, Culture, Sports, Science and Technology (MEXT) . ",

year = "2010",

month = may,

day = "12",

doi = "10.1016/j.tetlet.2010.03.014",

language = "English",

volume = "51",

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T1 - Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide

AU - Takamura, Hiroyoshi

AU - Kadonaga, Yuichiro

AU - Kadota, Isao

AU - Uemura, Daisuke

N1 - Funding Information: We are grateful to Dr. C. Han and Mr. Y. Yamano (Nagoya University) for the valuable discussions. We appreciate Okayama Foundation for Science and Technology, NOVARTIS Foundation (Japan) for the Promotion of Science, and WESCO Scientific Promotion Foundation for their financial supports. This research was supported by Grant-in-Aid for Young Scientists (B) ( 19710184 and 21710231 ) from Japan Society for the Promotion of Science (JSPS) and The Ministry of Education, Culture, Sports, Science and Technology (MEXT) .

PY - 2010/5/12

Y1 - 2010/5/12

N2 - Symbiodinolide is a polyol macrolide isolated from the marine dinoflagellate Symbiodinium sp. in 2007. The C14-C24 fragment of symbiodinolide possessing the 17R/18R/21R absolute configuration, which was obtained as one of the degraded products of symbiodinolide, was synthesized stereoselectively from cis-2-butene-1,4-diol. The detailed comparison of the synthetic product with the degraded product in the spectroscopic data confirmed that the stereostructure of the C14-C24 fragment was 17R, 18R, and 21R.

AB - Symbiodinolide is a polyol macrolide isolated from the marine dinoflagellate Symbiodinium sp. in 2007. The C14-C24 fragment of symbiodinolide possessing the 17R/18R/21R absolute configuration, which was obtained as one of the degraded products of symbiodinolide, was synthesized stereoselectively from cis-2-butene-1,4-diol. The detailed comparison of the synthetic product with the degraded product in the spectroscopic data confirmed that the stereostructure of the C14-C24 fragment was 17R, 18R, and 21R.

KW - Polyol macrolide

KW - Stereoselective synthesis

KW - Structural confirmation

KW - Symbiodinolide

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U2 - 10.1016/j.tetlet.2010.03.014

DO - 10.1016/j.tetlet.2010.03.014

M3 - Article

AN - SCOPUS:77950368428

VL - 51

SP - 2603

EP - 2605

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 19

ER -

Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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