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

8 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/chem.201503880

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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.",

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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.

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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DO - 10.1002/chem.201503880

M3 - Article

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VL - 22

SP - 1979

EP - 1983

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 6

ER -

Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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