Enantioselective total synthesis of (+)-rubrobramide, (+)-talaramide A, and (-)-berkeleyamide D by a skeletal diversification strategy
Enantioselective total synthesis of (+)-rubrobramide, (+)-talaramide A, and (-)-berkeleyamide D by a skeletal diversification strategy
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通过骨架多样化策略对映选择性全合成 ( )-rubrobramide、( )-talaramide A 和 (-)-berkeleyamide D
DOI：
10.1039/d1cc04290d
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发表时间：
2021
影响因子：
4.9
通讯作者：
Kogen Hiroshi
中科院分区：
文献类型：
--
作者：
Tanaka Kosaku;Kobayashi Kenichi;Kogen Hiroshi
通过基于区域选择性5-exo或6-endo环化的骨架多样化策略，从乙烯基酯实现了（+）-rubrobramide、（+）-talaramide A和（−）-berkeleyamide D的统一合成。本文首次报道了（+）-rubrobramide和（+）-talaramide A的对映选择性全合成。此外，合成的螺环内酰胺化合物，包括（-）-伯克利酰胺D，显示出对淀粉样蛋白-β聚集的中度抑制活性，用于治疗阿尔茨海默病。
A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5-exo or 6-endo cyclization. This report describes the first enantioselective total synthesis of (+)-rubrobramide and (+)-talaramide A. Additionally, synthetic spirocyclic lactam compounds, including (−)-berkeleyamide D, showed moderate inhibitory activity against amyloid-β aggregation for the potential treatment of Alzheimer's disease.