三原体的醇类化合物. (-) - - 尼特里姆 D 的总合成 D
Amos B Smith1, Naoki Kanoh, Haruaki Ishiyama
1Department of Chemistry, Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Journal of the American Chemical Society
|July 3, 2003
概括
研究人员实现了复杂的醇化物 (-) - penitrem D 的立体控制的总合成.这涉及关键结构特征的新方法,包括独特的自氧化用于震活动.
科学领域:
- 有机化学 有机化学
- 自然产品的合成自然产品的合成
- 药用化学 医学化学
背景情况:
- 印度醇类化合物,如penitrem D,是一种复杂的自然产品类.
- (-) -Penitrem D是一种发震的真菌毒素,具有复杂的分子结构.
- 这种复杂分子的总合成对于生物研究和模拟开发至关重要.
研究的目的:
- 为了实现 (-) - penitrem D. 的融合和立体控制的总合成.
- 开发适用于复杂的醇类化合物的新型合成方法.
- 引入关键的功能组对于震活动至关重要.
主要方法:
- 分子西半球的不对称合成.
- 在I环的立体声控制组装.
- 引入C(22) 三级基组的新型自氧化.
- 东半球和西半球的融合合使用一个定制的醇合成协议.
- A和F环的后期,立体选择性构造通过一个Sc(OTf) ((3-) 促进的级联.
主要成果:
- 成功合成了 (-) - - 尼特里姆 D. 的总合成.
- 关键结构图案的高效和立体控制的建设.
- 发现了一种用于三级酒精装置的新型自氧化反应.
- 开发一种新的醇合成协议.
- 为合成建立了一个43步最长的线性序列.
结论:
- 这项研究证明了一条可行且立体控制的通往 (-) - penitrem D. 的途径.
- 开发的合成策略为获取复杂的醇提供了有价值的工具.
- 引入C(22) 基组对于penitrem D.的震活性至关重要.
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