Catalytic Deoxygenative Transformation of Ketoacids/Esters for the Synthesis of Coumarin, Benzofuranone, and Dihydrobenzo[b]oxepin-2(3H)-one Derivatives,Advanced Synthesis & Catalysis

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Catalytic Deoxygenative Transformation of Ketoacids/Esters for the Synthesis of Coumarin, Benzofuranone, and Dihydrobenzo[b]oxepin-2(3H)-one Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-07-23 , DOI: 10.1002/adsc.202400505
Naveen Yadav ₁ , Jabir Khan ₁ , Chinmoy Hazra ₁

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We disclose herein a triflic acid and silane-promoted reductive deoxygenative transformation of ketoacid/esters for the divergent synthesis of different-sized lactones, which hold substantial significance in pharmaceutical and natural product chemistry. Owing to the simple reaction conditions and setup, this protocol features broad substrate generality, scalability, and good functional group tolerance, including late-stage functionalization of pharmaceutical compounds and natural products. The control experiments and detailed NMR study provide insight into the reaction mechanism.

中文翻译：

酮酸/酯的催化脱氧转化，用于合成香豆素、苯并呋喃酮和二氢苯并[b]氧杂平-2（3H）-酮衍生物

我们在此公开了一种三氟酸和硅烷促进的酮酸/酯的还原脱氧转化，用于不同大小的内酯的发散合成，这在制药和天然产物化学中具有重要意义。由于反应条件和设置简单，该方案具有广泛的底物通用性、可扩展性和良好的官能团耐受性，包括药物化合物和天然产物的后期官能化。对照实验和详细的 NMR 研究提供了对反应机制的见解。

更新日期：2024-07-23

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