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 the13C 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.
authors.affiliation: 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.
authors.forename: Hiroyoshi
authors.identifier: http://orcid.org/0000-0002-8330-969X
authors.initials: H
authors.lastname: Takamura
authors.affiliation: Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Fujiwara
authors.affiliation: Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
authors.forename: Yohei
authors.initials: Y
authors.lastname: Kawakubo
authors.affiliation: Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Kadota
authors.affiliation: Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka, 259-1293, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Uemura
keywords: macrocycles; natural products; polyols; stereoselective synthesis; structure elucidation