NDLI: Stereoselective Synthesis of the Proposed C79–C104 Fragment of Symbiodinolide

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Stereoselective Synthesis of the Proposed C79–C104 Fragment of Symbiodinolide

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Takamura, Hiroyoshi Uemura, Daisuke Kadota, Isao Kawakubo, Yohei Fujiwara, Takayuki
Description	Author Affiliation: Takamura H ( Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan. takamura@cc.okayama-u.ac.jp.); Fujiwara T ( Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.); Kawakubo Y ( Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.); Kadota I ( Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.); Uemura D ( Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka, 259-1293, Japan.)
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 $^{13}C NMR$ 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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	6
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-02-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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