(-) - 奥里多宁的总合成:中断的纳扎罗夫方法
Lingran Kong1, Fan Su1, Hang Yu1
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
Journal of the American Chemical Society
|December 6, 2019
概括
这项研究首次使用中断的纳扎罗夫反应对 (-) - 奥里多尼的选择性总合成. 这种新方法成功地构建了复杂的四环结构,包括具有挑战性的四级碳.
科学领域:
- 有机化学
- 合成化学
- 自然产品合成
背景情况:
- (-) - 奥里多宁是一种具有潜在生物活性的高度氧化的甲.
- 复杂的 (-) - 氨酸结构带来了重要的合成挑战,特别是多个立体中心和四级碳的存在.
研究的目的:
- 实现第一个反选择性 (-) - 氨酸的总合成.
- 开发一种新的合成策略,使用中断的纳扎罗夫反应来构建四环原子核.
主要方法:
- 乙选择性总合成
- 中断的纳扎罗夫反应
- 纳扎罗夫/霍索米-萨库莱布
- 环重新排列反应
- 最后阶段的氧化还原操作
主要成果:
- 成功构建了 (-) - 氨酸的四环骨架.
- 控制立体化学,包括挑战四级碳的形成.
- 高度氧化的甲结构的新合成.
结论:
- 开发的合成途径提供了有效的和对 (-) - 氨酸的选择性获取.
- 这项研究强调了中断纳扎罗夫反应在复杂分子合成中的有用性.
- 这项研究为进一步探索氨酸衍生物及其生物特性奠定了基础.
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