亚齐里丁的区域选择性环开口用于合成阿扎环
Nikhil Srivastava1, Hyun-Joon Ha1
1Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Republic of Korea.
Frontiers in chemistry
|November 6, 2023
概括
阿齐里丁环开放区域选择性根据替代剂不同. γ-基亚齐里丁在C2处开放,而γ-化亚齐里丁在C3处开放,产生罗利丁和皮佩里丁衍生物.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 异环化学 异环化学
背景情况:
- 亚齐里丁是有机合成中至关重要的紧张的三分子异环.
- 在阿齐里丁环开放反应中的区域选择性高度依赖基质结构和反应条件.
- 了解这些因素是控制复杂含化合物的合成的关键.
研究的目的:
- 研究不同功能组的亚齐里丁的区域选择性环开放反应.
- 探索g-和g-化替代剂对阿齐里丁活性的影响.
- 为了证明环开产品的后续循环化成为有价值的罗利丁和皮佩里丁支架.
主要方法:
- 亚齐里丁衍生物与特定的基替代剂 (γ-和γ-化) 的合成.
- 在酸性条件下 (三酸) 使用水作为基核的区域选择性环开放反应.
- 由此产生的中间体循环生成,形成替代的罗利丁和皮佩里丁环.
主要成果:
- 含有g-子替代剂的亚齐里丁在C2位置通过水的核友性攻击进行了区域选择性环开放.
- 具有g-silylated基组的亚齐里丁在C3位置呈现区域选择性环开口,涉及N1-C3键裂.
- 反应产物成功地循环生成替代的罗利丁和皮佩里丁衍生物,包括伪水素和单氨酸的类似物.
结论:
- 阿齐里丁环由基核友开放的区域选择性取决于基替代物的 γ 位置上的功能组的性质.
- 这项研究提供了一种通用的合成途径,通过受控的亚齐里丁环开放和随后的循环循环,到取代的罗利丁和皮佩里丁.
- 这些发现为药物和天然产品化学中复杂异环的有针对性的合成提供了宝贵的见解.
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