Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana 47907, United States.
Org Lett. 2020 Jul 2;22(13):5001-5004. doi: 10.1021/acs.orglett.0c01570. Epub 2020 Jun 17.
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 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.
生物碱包含具有不同结构骨架的家族成员。其中许多成员的特征是在其特征的 5-7-5 稠合三环核心中嵌入一个 γ-内酰胺环。在此，开发了一种吡咯策略，以实现三种生物碱的全合成：（±）stemoamide、（±）tuberostemoamide 和（±）sessilifoliamide A。在这些情况下，取代的吡咯被用作 γ-内酰胺前体。通过吡咯的连续氧化和烯酰胺的还原，在这三种天然产物中将吡咯转化为相应的 γ-内酰胺。在合成的早期阶段使用吡咯具有通过利用其亲核性快速构建关键中间体的优势。
