Synthesis and structural determination of the C33-C42 fragment of symbiodinolide

Hiroyoshi Takamura; Yuichiro Kadonaga; Yoshi Yamano; Chunguang Han; Yoko Aoyama; Isao Kadota; Daisuke Uemura

doi:10.1016/j.tetlet.2008.11.056

Synthesis and structural determination of the C33-C42 fragment of symbiodinolide

Hiroyoshi Takamura, Yuichiro Kadonaga, Yoshi Yamano, Chunguang Han, Yoko Aoyama, Isao Kadota, Daisuke Uemura

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

20 Citations (Scopus)

Abstract

Symbiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S).

Original language	English
Pages (from-to)	863-866
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.056
Publication status	Published - Feb 25 2009

Keywords

Absolute configuration
Chemical synthesis
Cross-metathesis degradation
Polyol macrolide
Symbiodinolide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.11.056

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title = "Synthesis and structural determination of the C33-C42 fragment of symbiodinolide",

abstract = "Symbiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S).",

keywords = "Absolute configuration, Chemical synthesis, Cross-metathesis degradation, Polyol macrolide, Symbiodinolide",

author = "Hiroyoshi Takamura and Yuichiro Kadonaga and Yoshi Yamano and Chunguang Han and Yoko Aoyama and Isao Kadota and Daisuke Uemura",

note = "Funding Information: We thank Okayama Foundation for Science and Technology and The Naito Foundation for their financial supports. This research was partially supported by Grant-in-Aid for Scientific Research from MEXT, Japan.",

year = "2009",

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doi = "10.1016/j.tetlet.2008.11.056",

language = "English",

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T1 - Synthesis and structural determination of the C33-C42 fragment of symbiodinolide

AU - Takamura, Hiroyoshi

AU - Kadonaga, Yuichiro

AU - Yamano, Yoshi

AU - Han, Chunguang

AU - Aoyama, Yoko

AU - Kadota, Isao

AU - Uemura, Daisuke

N1 - Funding Information: We thank Okayama Foundation for Science and Technology and The Naito Foundation for their financial supports. This research was partially supported by Grant-in-Aid for Scientific Research from MEXT, Japan.

PY - 2009/2/25

Y1 - 2009/2/25

N2 - Symbiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S).

AB - Symbiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S).

KW - Absolute configuration

KW - Chemical synthesis

KW - Cross-metathesis degradation

KW - Polyol macrolide

KW - Symbiodinolide

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

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Synthesis and structural determination of the C33-C42 fragment of symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

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