Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide

Hiroyoshi Takamura; Takayuki Fujiwara; Yohei Kawakubo; Isao Kadota; Daisuke Uemura

doi:10.1002/chem.201503880

Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide

Hiroyoshi Takamura, Takayuki Fujiwara, Yohei Kawakubo, Isao Kadota, Daisuke Uemura

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

6 Citations (Scopus)

Abstract

Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the ¹³C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.

Original language	English
Pages (from-to)	1979-1983
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	6
DOIs	https://doi.org/10.1002/chem.201503880
Publication status	Published - Feb 5 2016

Keywords

macrocycles
natural products
polyols
stereoselective synthesis
structure elucidation

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Organic Chemistry

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title = "Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide",

abstract = "Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.",

keywords = "macrocycles, natural products, polyols, stereoselective synthesis, structure elucidation",

author = "Hiroyoshi Takamura and Takayuki Fujiwara and Yohei Kawakubo and Isao Kadota and Daisuke Uemura",

note = "Funding Information: We are grateful to the Division of Instrumental Analysis, Okayama University, for the NMR measurements. We appreciate the JGC-S Scholarship Foundation, The Naito Foundation, The Sumitomo Foundation, and The Uehara Memorial Foundation for their financial support. This research was supported by a Grant-in Aid for Scientific Research (no. 24710250) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

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doi = "10.1002/chem.201503880",

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AU - Takamura, Hiroyoshi

AU - Fujiwara, Takayuki

AU - Kawakubo, Yohei

AU - Kadota, Isao

AU - Uemura, Daisuke

N1 - Funding Information: We are grateful to the Division of Instrumental Analysis, Okayama University, for the NMR measurements. We appreciate the JGC-S Scholarship Foundation, The Naito Foundation, The Sumitomo Foundation, and The Uehara Memorial Foundation for their financial support. This research was supported by a Grant-in Aid for Scientific Research (no. 24710250) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/2/5

Y1 - 2016/2/5

N2 - Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.

AB - Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.

KW - macrocycles

KW - natural products

KW - polyols

KW - stereoselective synthesis

KW - structure elucidation

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

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ER -

Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

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