达福德胺B和达福德胺B乳的总合成
Lian-Dong Guo1, Jieping Hou1, Wentong Tu1
1Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , China.
Journal of the American Chemical Society
|July 13, 2019
概括
研究人员首次实现了复杂的Daphniphyllum甲基Dapholdhamine B的选择性合成. 这一突破为天然产品提供了新的合成途径.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 达非类因其结构复杂性和显著的生物活性而闻名.
- 达胺B中独特的aza-adamantane核心和多个立体中心带来了相当大的合成挑战.
研究的目的:
- 报告天然产品达福德B的第一个反选择性总合成.
- 制定一个简洁而有效的合成策略,
主要方法:
- 作为一个关键步骤,
- 采用了α--α,β-不和的优化合成.
- 嵌入基质依赖的分子内阿扎-迈克尔添加和胺激活以取消.
主要成果:
- 成功合成了达胺B及其乳衍生物.
- 建立了一个简短的合成路线,其中包括8个连续的立体中心,其中包括3个完全替代的.
- 证明了关键的转化,包括SN2'-类型的乳化和Horner-Wadsworth-Emmons的化.
结论:
- 开发的合成方法代表了aza-adamantane天然产品的首次全合成.
- 这项工作为访问复杂的化物结构提供了有价值的方法.
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