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Pyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A.
Organic Letters ( IF 5.2 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.orglett.0c01570 Xianglin Yin 1 , Kaiqing Ma 1 , Ying Dong 1 , Mingji Dai 1
Organic Letters ( IF 5.2 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.orglett.0c01570 Xianglin Yin 1 , Kaiqing Ma 1 , Ying Dong 1 , Mingji Dai 1
Affiliation
Stemona alkaloids contain family members with diverse structural scaffolds. Many of them feature a γ-lactam ring embedded in their characteristic 5–7–5 fused tricyclic core. Herein a pyrrole strategy was developed to enable the total syntheses of three Stemona alkaloids: (±)stemoamide, (±)tuberostemoamide, and (±)sessilifoliamide A. In these cases, a substituted pyrrole was used as the γ-lactam precursor. A sequential pyrrole oxidation and enamide reduction were realized to convert the pyrrole to the corresponding γ-lactam in those three natural products. The use of a pyrrole in an early stage of the synthesis offers the advantage of rapid construction of the key intermediates by exploiting its nucleophilicity.
中文翻译:
含γ-内酰胺的Stemona生物碱的吡咯策略:(±)硬脂酰胺,(±)Tuberostemoamide和(±)Sessilifoliamide A.
肉豆蔻生物碱包含具有不同结构支架的家族成员。他们中的许多人都在其特有的5–7–5稠合三环核中嵌入了γ-内酰胺环。在本文中,开发了吡咯策略以实现三种Stemona生物碱的整体合成:(±)硬脂酰胺,(±)结核菌酰胺和(±)倍半硅酰胺A。在这些情况下,将取代的吡咯用作γ-内酰胺前体。实现了连续的吡咯氧化和酰胺还原,以将这三种天然产物中的吡咯转化为相应的γ-内酰胺。在合成的早期使用吡咯具有通过利用亲核性快速构建关键中间体的优势。
更新日期:2020-07-02
中文翻译:
含γ-内酰胺的Stemona生物碱的吡咯策略:(±)硬脂酰胺,(±)Tuberostemoamide和(±)Sessilifoliamide A.
肉豆蔻生物碱包含具有不同结构支架的家族成员。他们中的许多人都在其特有的5–7–5稠合三环核中嵌入了γ-内酰胺环。在本文中,开发了吡咯策略以实现三种Stemona生物碱的整体合成:(±)硬脂酰胺,(±)结核菌酰胺和(±)倍半硅酰胺A。在这些情况下,将取代的吡咯用作γ-内酰胺前体。实现了连续的吡咯氧化和酰胺还原,以将这三种天然产物中的吡咯转化为相应的γ-内酰胺。在合成的早期使用吡咯具有通过利用亲核性快速构建关键中间体的优势。