Total synthesis and structure revision of chrysamide B

Total synthesis and structure revision of chrysamide B

Total synthesis of the originally proposed chrysamide B ( 2 ) is described, which features a convergent assembly of the chiral piperazine core and epoxy-acid. Mismatched spectroscopic data for the synthetic sample compared to that for the isolate led us to propose the revised structure 3 based on bi...

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Veröffentlicht in:Organic Chemistry Frontiers 2018-12, Vol.5 (23), p.3402-3405
Hauptverfasser: Chen, Jinhong, Li, Junfang, Zhu, Longqing, Peng, Xue, Feng, Yiyue, Lu, Yingmei, Hu, Xiaoling, Liang, Jianpin, Zhao, Quanyi, Wang, Zhen
Format: Artikel
Sprache:eng
Schlagworte:
Crystallography
Organic chemistry
Piperazine
Synthesis
X ray spectra
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Zusammenfassung:Total synthesis of the originally proposed chrysamide B ( 2 ) is described, which features a convergent assembly of the chiral piperazine core and epoxy-acid. Mismatched spectroscopic data for the synthetic sample compared to that for the isolate led us to propose the revised structure 3 based on biosynthetic considerations. In a further antibacterial assay, chrysamide B and its diastereomer 2 exhibited different activities.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/C8QO00949J