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Atroposelective Total Synthesis of Cihunamide B
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-01-19 , DOI: 10.1021/jacs.3c11016
Longhui Yu 1 , Yuuya Nagata 2 , Hugh Nakamura 1
Affiliation  

A short, atroposelective synthesis of cihunamide B (1) is reported. The feature of this report is the decagram-scale SNAr reaction of l-tryptophan derivatives, followed by atroposelective Larock macrocyclization. This strategy allowed the construction of a Trp-Trp cross-linkage with unprecedented atropisomerism. The atroposelectivity of this Larock macrocyclization has been investigated through a combination of experimental and computational chemistry, yielding detailed insights into the synthesis of biaryl linkages. It also enabled the concise synthesis of cihunamide B (1), which is expected to be a potential antibacterial agent.

中文翻译:


Cihunamide B 的肌体选择性全合成



报道了cihunamide B ( 1 ) 的简短、间质选择性合成。该报告的特点是L-色氨酸衍生物的十克规模的SN Ar反应,然后是atroposelective Larock大环化。该策略允许构建具有前所未有的阻转异构性的色氨酸-色氨酸交联。通过实验和计算化学的结合,研究了这种 Larock 大环化的间质选择性,从而对联芳基键的合成产生了详细的见解。它还能够简明合成cihunamide B ( 1 ),该化合物有望成为一种潜在的抗菌剂。
更新日期:2024-01-19
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