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阿普利西阿斯醇A的总合成
Zhaohong Lu1, Xiang Zhang1, Zhicong Guo1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|June 26, 2018
概括
研究人员报告了第一次非对称的Aplysiasecosterol A的总合成,这是一种来自海Aplysia kurodai的独特二氧化. 这一成就为这种复杂的海洋天然产品提供了新的合成途径.
科学领域:
- 有机化学
- 海洋天然产品化学
- 合成化学
背景情况:
- 阿普利西亚醇A (1) 是一个结构独特的9,11-二类固醇.
- 这个化合物最初是从海Aplysia kurodai中分离出来的.
- 这种复杂的海洋天然产品的总合成带来了重大挑战.
研究的目的:
- 实现第一个非对称的AplysiasecosterolA (1) 总合成.
- 开发高效和融合的合成策略来获取这种不寻常的二氧化.
- 探索新的方法来构建化合物1的复杂立体化学特征.
主要方法:
- 融合合成的战略.
- 左侧部分的脱对称缩小,化和根基循环.
- 不对称的2-化和非对称的乳化,以获得高效的细分.
- 迈尔斯化,苏苏基-米亚乌拉合,阿加瓦尔化-化,以及左侧部分的兹韦菲尔-埃文斯化.
- 碎片合的Reformatsky类反应
- 以铁为媒介,以原子转移为基础的基质循环,用于立体中心生成.
主要成果:
- 成功和不对称的Aplysiasecosterol A (1) 的总合成
- 左侧部分与三个相邻的立体中心的构造.
- 通过两个不同的合成路径准备右侧部分.
- 两个碎片的有效合.
- 在中央域内连续生成三个立体中心的立体选择性生成.
结论:
- 已经完成了第一次非对称的Aplysiasecosterol A的总合成.
- 开发的融合策略为这种结构异常的二氧化提供了有效的途径.
- 合成方法突出了构建复杂立体化学架构的新方法.
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