Total Synthesis of Acaulide and Acaulone A.,Organic Letters

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Total Synthesis of Acaulide and Acaulone A.
Organic Letters ( IF 4.9 ) Pub Date : 2020-07-03 , DOI: 10.1021/acs.orglett.0c01907
Jun Hirabayashi ₁ , Fumika Yakushiji _{1,

2} , Akira Katsuyama _{1,

2} , Satoshi Ichikawa _{1,

2,

3}

Affiliation

Acaulide and acaulone A, which contain 14-membered macrodiolides, were isolated from a culture of Acaulium sp. H-JQSF. The antiosteoporosis activity of acaulide is expected to contribute to drug discovery research for an aging society. We herein report the first total synthesis of acaulide, acaulone A, and 10-keto-acaudiol A. Acaulide and acaulone A were synthesized via the late stage Michael addition to the 14-membered macrodiolide, which was inspired by plausible biosynthetic pathways. This approach succeeded in the construction of the acaulide skeleton, which revealed the specific conformation of the 14-membered macrodiolide for late stage functionalization.

中文翻译：

丙烯酰胺和Acaulone A的全合成

从Acaulium sp。的培养物中分离出含有14元大环氧化物的Acaulide和acauloneA 。H-JQSF。阿拉伯胶的抗骨质疏松活性有望为老龄化社会的药物发现研究做出贡献。我们在本文中报告了阿拉伯胶，阿拉伯胶A和10-酮-音频的第一全合成。丙烯酰胺和阿拉伯胶A是通过后期迈克尔加成到14元大环己二醇中而合成的，这受到可能的生物合成途径的启发。该方法成功地构建了阿拉伯胶化物骨架，该骨架揭示了用于后期功能化的14元大环氧化物的特定构象。

更新日期：2020-07-17

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