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

Chemistry. 2016 Feb;22(6):1979-1983. doi: 10.1002/chem.201503880. Epub 2015 Dec 11.

Authors

Hiroyoshi Takamura¹, Takayuki Fujiwara², Yohei Kawakubo², Isao Kadota², Daisuke Uemura³

Affiliations

¹ 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.
² Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
³ Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka, 259-1293, Japan.

PMID: 26661715
DOI: 10.1002/chem.201503880

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.

Keywords: macrocycles; natural products; polyols; stereoselective synthesis; structure elucidation.