Stereoselective Synthesis of the Proposed C79–C104 Fragment of Symbiodinolide |
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| Authors: | Prof?Dr Hiroyoshi Takamura Takayuki Fujiwara Yohei Kawakubo Prof?Dr Isao Kadota Prof?Dr Daisuke Uemura |
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| Affiliation: | 1. Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, Kita-ku, Okayama, Japan;2. Department of Chemistry, Faculty of Science, Kanagawa University, Hiratsuka, Japan |
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| 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. |
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| Keywords: | macrocycles natural products polyols stereoselective synthesis structure elucidation |
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