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An Intramolecular Diels−Alder Approach to AZD8154

有机合成与工艺文献分享 2024-12-04 07:48
文章摘要
本文介绍了一种新的内分子Diels-Alder反应途径，用于合成双磷酸肌醇3-激酶γδ抑制剂AZD8154的异吲哚啉酮核心结构。该方法在开发过程中为首次人体试验（FIH）及后续提供了多公斤级供应。研究中，通过使用过量DIPEA生成胺8·HCl的游离碱，随后加入9，快速形成了环加成产物6，纯化后产率为78%。此外，使用Lewis酸BF3·Et2O导致完全消耗起始材料，但主要生成芳香化产物10，这是由于硫酮基团的迁移。尽管该基本条件在文献中未见报道，但研究者推测硫酮的吸电子性质可能促进氧桥的β-消除。总体上，该路线在38%的产率下完成了AZD8154异吲哚啉酮核心的合成，步骤少于10步，满足了路线设计要求。
An Intramolecular Diels−Alder Approach to AZD8154
查看文献： An Intramolecular Diels–Alder Approach to the Isoindolinone Core of AZD8154
查看期刊：Organic Process Research & Development
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