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作为Synthons的直角保护的Diaminocyclopentenones: (±) -Agelastatin A的总合成

Rafael F A Gomes¹, João R Vale¹, Juliana G Pereira¹

¹Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Avenida Professor Gama Pinto, 1649-003 Lisbon, Portugal.

Organic letters

|May 30, 2023

概括

研究人员开发了一种新的方法,用受保护的氨基酸合成氨基cyclopentane构建块. 这种多功能合成物促进了复杂分子合成,其在制造 (±) -Agelastatin A.中使用证明了这一点.

科学领域:

有机化学有机化学
合成化学合成化学
自然产品的合成自然产品的合成

背景情况:

氨基cyclopentanes 在生物活性天然产品中普遍存在.
开发多功能合成子对于复杂分子的总合成至关重要.
正角保护策略可以实现选择性功能化.

研究的目的:

为了准备一个新的synthon的总合成特色正角保护的氨基.
建立一种可靠的合成trans-4,5-diaminocyclopentenones的方法.
为了证明开发的synthon在合成复杂的自然产品中的实用性.

主要方法:

混合的trans-4,5-diaminocyclopentenones是由furfural和两个胺基合成的.
铜(II) 三叶酸 (Cu(OTf) 2) 被用作反应的催化剂.
在选择性氨基基修饰中采用了正对角脱保护策略.

主要成果:

建立了一条新合成路径,以对直角保护的氨基cyclopentane synthons.
合成的米诺cyclopentenones具有可选择性去保护的氨基群.
通过 (±) -Agelastatin A.的总合成来验证synthon的实用性.

结论:

开发的方法为访问复杂的氨基cyclopentane衍生物提供了一个有价值的工具.
正交保护的synthon可以实现高效和选择性的修改.
这种方法对 (±) -Agelastatin A.等天然产品的总合成有显著的贡献.

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