Stereoselective synthesis of the C94-C104 fragment of symbiodinolide

Hiroyoshi Takamura; Kosuke Tsuda; Yohei Kawakubo; Isao Kadota; Daisuke Uemura

doi:10.1016/j.tetlet.2012.06.005

Stereoselective synthesis of the C94-C104 fragment of symbiodinolide

Hiroyoshi Takamura, Kosuke Tsuda, Yohei Kawakubo, Isao Kadota, Daisuke Uemura

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

10 Citations (Scopus)

Abstract

Stereoselective synthesis of the C94-C104 fragment of symbiodinolide which is a polyol marine natural product with a molecular weight of 2860 has been accomplished. The synthetic route features Achmatowicz rearrangement and RuO ₄-catalyzed dihydroxylation for the construction of the tetrahydropyran moiety and the dithiane addition to the aldehyde for the introduction of the side chain.

Original language	English
Pages (from-to)	4317-4319
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.005
Publication status	Published - Aug 15 2012

Keywords

Achmatowicz rearrangement
Dithiane addition
Polyol marine natural product
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.2012.06.005

Cite this

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title = "Stereoselective synthesis of the C94-C104 fragment of symbiodinolide",

abstract = "Stereoselective synthesis of the C94-C104 fragment of symbiodinolide which is a polyol marine natural product with a molecular weight of 2860 has been accomplished. The synthetic route features Achmatowicz rearrangement and RuO 4-catalyzed dihydroxylation for the construction of the tetrahydropyran moiety and the dithiane addition to the aldehyde for the introduction of the side chain.",

keywords = "Achmatowicz rearrangement, Dithiane addition, Polyol marine natural product, Symbiodinolide",

author = "Hiroyoshi Takamura and Kosuke Tsuda and Yohei Kawakubo and Isao Kadota and Daisuke Uemura",

note = "Funding Information: We appreciate the Kato Memorial Bioscience Foundation, The Research Foundation for Pharmaceutical Sciences, The Society of Synthetic Organic Chemistry, Japan (Shionogi Award in Synthetic Organic Chemistry, Japan), and The Asahi Glass Foundation for their financial supports. This research was supported by Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

year = "2012",

month = aug,

day = "15",

doi = "10.1016/j.tetlet.2012.06.005",

language = "English",

volume = "53",

pages = "4317--4319",

journal = "Tetrahedron Letters",

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T1 - Stereoselective synthesis of the C94-C104 fragment of symbiodinolide

AU - Takamura, Hiroyoshi

AU - Tsuda, Kosuke

AU - Kawakubo, Yohei

AU - Kadota, Isao

AU - Uemura, Daisuke

N1 - Funding Information: We appreciate the Kato Memorial Bioscience Foundation, The Research Foundation for Pharmaceutical Sciences, The Society of Synthetic Organic Chemistry, Japan (Shionogi Award in Synthetic Organic Chemistry, Japan), and The Asahi Glass Foundation for their financial supports. This research was supported by Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

PY - 2012/8/15

Y1 - 2012/8/15

N2 - Stereoselective synthesis of the C94-C104 fragment of symbiodinolide which is a polyol marine natural product with a molecular weight of 2860 has been accomplished. The synthetic route features Achmatowicz rearrangement and RuO 4-catalyzed dihydroxylation for the construction of the tetrahydropyran moiety and the dithiane addition to the aldehyde for the introduction of the side chain.

AB - Stereoselective synthesis of the C94-C104 fragment of symbiodinolide which is a polyol marine natural product with a molecular weight of 2860 has been accomplished. The synthetic route features Achmatowicz rearrangement and RuO 4-catalyzed dihydroxylation for the construction of the tetrahydropyran moiety and the dithiane addition to the aldehyde for the introduction of the side chain.

KW - Achmatowicz rearrangement

KW - Dithiane addition

KW - Polyol marine natural product

KW - Symbiodinolide

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DO - 10.1016/j.tetlet.2012.06.005

M3 - Article

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VL - 53

SP - 4317

EP - 4319

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Stereoselective synthesis of the C94-C104 fragment of symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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