Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide

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

doi:10.1016/j.tet.2009.07.019

Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide

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

School of Science

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

22 Citations (Scopus)

Abstract

Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S).

Original language	English
Pages (from-to)	7449-7456
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2009.07.019
Publication status	Published - Sept 5 2009

Keywords

Absolute configuration
Chemical synthesis
Cross-metathesis degradation
Symbiodinolide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.07.019

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title = "Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide",

abstract = "Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S).",

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

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

note = "Funding Information: We are grateful to Ms. Yoko Aoyama for her early contribution. We appreciate Okayama Foundation for Science and Technology, NOVARTIS Foundation (Japan) for the Promotion of Science, and The Mitsubishi Foundation for their financial supports. This research was partially supported by Grant-in-Aid for Scientific Research (19710184, 21710231, and 16GS0206) from the Japan Society for the Promotion of Science.",

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doi = "10.1016/j.tet.2009.07.019",

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AU - Takamura, Hiroyoshi

AU - Kadonaga, Yuichiro

AU - Yamano, Yoshi

AU - Han, Chunguang

AU - Kadota, Isao

AU - Uemura, Daisuke

N1 - Funding Information: We are grateful to Ms. Yoko Aoyama for her early contribution. We appreciate Okayama Foundation for Science and Technology, NOVARTIS Foundation (Japan) for the Promotion of Science, and The Mitsubishi Foundation for their financial supports. This research was partially supported by Grant-in-Aid for Scientific Research (19710184, 21710231, and 16GS0206) from the Japan Society for the Promotion of Science.

PY - 2009/9/5

Y1 - 2009/9/5

N2 - Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S).

AB - Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S).

KW - Absolute configuration

KW - Chemical synthesis

KW - Cross-metathesis degradation

KW - Symbiodinolide

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Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

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