(-) - 皮里米多布兰酸和P-3A的总合成
Adam S Duerfeldt1, Dale L Boger
1Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Journal of the American Chemical Society
|January 14, 2014
概括
研究人员使用强大的反向电子需求迪尔斯-阿尔德反应开发了 (-) - 皮里米多布兰酸和P-3A的新合成方法. 这种方法有效地创建了胺核,并在一个步骤中引入立体化学,使模拟合成成为可能.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- (-) 胺酸和P-3A是具有潜在生物活性的复杂天然产品.
- 有效和立体选择性合成路径对于访问这些分子及其类型至关重要.
研究的目的:
- 开发 (-) - 皮里米多布兰酸和P-3A的融合总合成.
- 建立一种多功能方法来合成这些天然产品的改性类似物.
主要方法:
- 利用了缺电子的1,2,3-triazines和一种性初级阿米丁之间的反向电子需求迪尔斯-阿尔德反应.
- 采用了融合合成策略,允许对类似物进行晚期分离合成.
主要成果:
- 成功合成了 (-) - 皮里米多胺酸和P-3A.
- 证明了迪尔斯-阿尔德反应的区域选择性是强大的,即使在triazine上有电子吸收组.
- 建立了一种方法,在单个循环加法步骤中引入所有必要的立体化学.
结论:
- 开发的反向电子需求迪尔斯-阿尔德反应是胺合成的强大工具.
- 收的方法促进了创建不同的类似物,在皮里米丁核心或侧链的修改.
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