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呋甾皂苷的全合成及结构确证。

Total Synthesis and Structure Confirmation of Fusaroside.

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

出版信息

J Org Chem. 2023 Jul 7;88(13):8175-8178. doi: 10.1021/acs.joc.3c00167. Epub 2023 Jun 8.

Abstract

Recently, we synthesized the proposed structure of the fungal glycolipid fusaroside and suggested corrections in its structure with respect to the positions of the double bonds in the lipid portion. Herein, we report the first total synthesis of the proposed revised structure of fusaroside and thereby confirm its structure. The synthesis involved Julia-Kocienski olefination for the construction of fatty acid and its coupling with trehalose at the O4 position followed by late-stage gem-dimethylation as key steps.

摘要

最近,我们合成了真菌糖脂绵子糖脂的建议结构,并就脂质部分双键的位置对其结构提出了修正。在此,我们报告了绵子糖脂建议修订结构的首次全合成,从而确定了其结构。该合成涉及 Julia-Kocienski 烯烃化反应构建脂肪酸,以及在 O4 位与海藻糖偶联,随后进行晚期的偕二甲基化为关键步骤。

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