乙选择性 (+) - 氨酸的总合成
Kyle J Cassaidy1, Viresh H Rawal1
1Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
研究人员开发了一种使用过渡金属催化 [2+2+2] 循环异构的新合成策略,以获取Veratrum类. 这种高效的方法使得海洛因在21个步骤内首次完全合成.
科学领域:
- 有机化学
- 整体综合
- 医学化学
背景情况:
- 过渡金属催化 [2+2+2] 循环异构化是构建复杂分子结构的强大工具.
- 维拉特是一种具有潜在治疗用途的重要天然产品.
- 为了进一步研究,开发高效和融合的合成途径至关重要.
研究的目的:
- 建立一种新且高度融合的合成策略,用于新建Veratrum类.
- 证明分子内 [2+2+2] 循环聚合在组装复杂的六环素骨架中的实用性.
- 为了实现第一个完全合成的海洛因.
主要方法:
- 包含类固醇A/B环的二烯片段的酶选择性合成.
- 一个用propargyl替代的piperidinone (F环) 单元的不对称合成.
- 高产量的碎片合,然后进行分子内 [2+2+2] 循环异构,形成C/D/E环.
- 为最终产品形成的后期功能化.
主要成果:
- 成功开发了一种融合合成策略,利用关键的分子内 [2+2+2] 循环聚合.
- 该策略有效地在一个步骤中构建了六环胺核心结构.
- 从乙烯基乙烯基完成了第一个全合成的21步骤.
结论:
- 报告的策略为Veratrum类物提供了新的有效途径.
- 内分子 [2+2+2] 循环异构化是构建复杂多环系统的高效方法.
- 这项工作显著提升了复杂自然产品的总合成.
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